Hydroximic acid halogenides, method for the production and use thereof

ABSTRACT

Hydroximic acid halides of the formula I                    
     where the substituents have the following meanings: 
     X is NOCH 3 , CHOCH 3  or CHCH 3 ; 
     Y is O or NH; 
     R 1  is halogen; 
     R 2  is unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl or aryl; 
     R 3  is unsubstituted or substituted alkyl, alkoxyalkyl, cycloalkyl-alkyl, alkenyl and alkynyl, 
     their salts, processes for their preparation, and their use.

This application is a 371 of PCT/EP98/00782 filed Feb. 12, 1998.

TECHNICAL FIELD

The present invention relates to hydroximic acid halides of the formula I

where the substituents have the following meanings:

X is NOCH₃, CHOCH₃ or CHCH₃;

Y is O or NH;

R¹ is halogen;

R² is C₂-C₆-alkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl, it being possible for these groups to be partially or fully halogenated and/or to have attached to them one or two of the following radicals: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and phenyl, it being possible for the phenyl, in turn, to be partially or fully halogenated and/or to have attached to it one to three of the following groups: cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

methyl which is partially or fully halogenated and/or has attached to it one of the following radicals: cyano, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

C₅-C₆-cycloalkyl which can be partially or fully halogenated and/or can have attached to it one to three C₁-C₄-alkyl groups;

aryl or arylmethylene which can be partially or fully halogenated in the aryl moiety and/or can have attached to it one to three of the following radicals: cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

R³ is C₁-C₆-alkyl, C₁-C₃-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₃-C₆-alkenyl and C₃-C₆-alkynyl, it being possible for these groups to be partially or fully halogenated and it being possible for the cycloalkyl groups additionally to have attached to them one to three C₁-C₄-alkyl radicals,

and to the salts thereof.

Furthermore the invention relates to processes for the preparation of the compounds I, to compositions comprising them and to their use for controlling animal pests and harmful fungi.

BACKGROUND ART

Phenylacetic acid derivatives which act against animal pests and harmful fungi and whose general structure embraces the structure of the present compounds are known from the literature (WO-A 95/21,153; WO-A 95/21,154). Moreover, WO-A 95/18,789 describes compounds of similar structures which are active against animal pests and harmful fungi.

Against this background, it was an object of the present invention to provide compounds which have improved properties regarding their action.

We have found that this object is achieved by the compounds I defined at the outset. Moreover, there have been found processes and intermediates for their preparation, compositions comprising them, and their use against animal pests and harmful fungi.

The present compounds I differ from the compounds known from WO-A 95/21,153 and WO-A 95/21,154 by the particular combination of the groups R¹ to R³. In particular, it has been found that compounds of the known structural type have an improved activity when a halogen is bonded in the position of the radical R¹ and a sterically demanding group which increases the lipophilicity of the compound is bonded in the position of the radical R², and when the position of the radical R³ is not taken up by hydrogen.

DISCLOSURE OF INVENTION

In general, the compounds I can be obtained by the processes described in the literature cited at the outset.

The compounds I are especially advantageously obtained by first converting a carboxylic ester IIa with hydroxylamine to give the corresponding hydroxamic acid IIc, subsequently reacting IIc with a benzyl compound IIIa to give the corresponding hydroxamic ester IV and converting IV with a halogenating agent [HAL] to give I.

R^(x) in formula IIa is the radical of a customary leaving group. Customary leaving groups for the purposes of the present reaction are to be understood as meaning especially the following groups: C₁-C₄-alkyl (especially methyl or ethyl) or phenyl.

L in formula IIIa is a nucleofugic leaving group. For the purposes of the present reaction, this is to be understood as meaning especially the following: halogen, alkyl sulfonate or aryl sulfonate, especially chlorine, bromine, iodine, mesylate, tosylate and triflate.

The reaction of the carboxylic ester IIa with hydroxylamine is normally carried out at from −20° C. to 50° C., preferably 0° C. to 20° C., in an inert organic solvent, preferably in the presence of a base (cf. literature: Houben-Weyl, 4th Edition, Vol. E5, p. 1141 et seq.).

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitrites such as acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably alcohols such as methanol and ethanol. Mixtures of these may also be used.

Bases which are generally suitable are inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and also alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, and furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. The following are especially preferred: alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and also alkali metal alkoxides such as sodium methoxide and sodium ethoxide.

In general, the bases are used in equimolar amounts or in an excess.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ an excess of hydroxylamine based on IIa.

The carboxylic esters IIa required for the preparation of the compounds I which are not already known from the literature [DE-A 28 08 317; DE-A 22 65 234; J. Chem. Soc. PT 1 (1975), 2340 et seq.; Chem. Ber. 16 (1883), 2987 et seq.; J. Org. Chem. 37 (1972), 139] can be prepared in accordance with the literature cited.

The reaction of the hydroxamic acid IIc with the benzyl compound IIIa is normally carried out at from 0° C. to 130° C., preferably 10° C. to 60° C., in an inert organic solvent in the presence of a base [cf. literature: Liebigs Ann. Chem. 1992, 997 et seq.; Synth. Commun. 19, (1989), 339 et seq.].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably tetrahydrofuran, acetonitrile and dimethylformamide. Mixtures of these may also be used.

Bases which are generally suitable are inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal hydrides and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride, alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, and furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. The following are especially preferred: sodium methoxide, potassium carbonate and sodium hydride.

In general, the bases are used in equimolar amounts or in an excess or, if appropriate, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ an excess of IIc based on IIIa.

Those benzyl compounds required for this reaction which are not known from the literature cited at the outset can be prepared in accordance with this literature.

The halogenation of the hydroxamic esters IV is normally carried out at from −20° C. to 100° C., preferably −10° C. to 80° C., in an inert organic solvent [cf. literature: Houben-Weyl, 4th Edition, Vol. E5, p. 631 et seq.; J. Org. Chem. 36 (1971), 233; Synthesis 9 (1991), 750 et seq.; Tetrahedron 52(1) (1996), 233 et seq.].

Halogenating agents which are suitable for this reaction are the customary inorganic and organic halogenating agents, eg. thionyl chloride, oxalyl chloride, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, phosphorus triiodide, triphenylphosphine/CCl₄, triphenylphosphine/CBr₄, triphenylphosphine/iodine, preferably thionyl chloride or the abovementioned triphenylphosphine reagents.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably acetonitrile, toluene and tetrahydrofuran. Mixtures of these may also be used.

The halogenating agents are generally employed in at least equimolar amounts. It may be advantageous for the yield to employ them in an excess of up to 10 mol based on 1 mol of IV, preferably up to 5 mol, in particular up to 3 mol.

Alternatively, the compounds IV can also be obtained by reacting a carboxylic acid IIb with a benzylhydroxylamine IIIb.

This reaction is normally carried out at from −10° C. to 120° C., preferably 0° C. to 50° C., in an inert organic solvent in the presence of an activating reagent [cf. literature: Houben-Weyl, 4th Ed. Vol. E5 p. 1141 et seq.; J. Antibiot. 39 (1986), 1382].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably tetrahydrofuran and methylene chloride. Mixtures of these may also be used.

Suitable activating reagents are acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, thionyl chloride or oxalyl chloride; anhydride formers such as ethyl chloroformate or methanesulfonyl chloride; carbodiimides such as N,N′-dicyclohexylcarbodiimide or other customary agents such as N,N′-carbonyldiimidazole or triphenylphosphine in CCl₄. The following are especially preferred: thionyl chloride, oxalyl chloride and N,N′-carbonyldiimidazole.

In general, the activating reagents are used in equimolar amounts or in excess.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ an excess of IIb based on IIIb.

Those carboxylic acids IIb required for this reaction which are not already known from the literature [J. Pharm. Sci. 57 (1968), 688 et seq.; DE-A 22 23 375; DE-A 22 65 234] can be prepared in accordance with the literature cited.

Moreover, the compounds IV are also obtained by reacting a carboxylic ester of the formula IIa with the benzylhydroxylamine IIIb under the conditions described above for the reaction of IIa to IIc.

In a further process, the compounds I are advantageously obtained by converting an amidoxime IId with a benzyl compound IIIa to give the corresponding compound of the formula V and exchanging the amino group of V for halogen via a diazotization reaction.

The reaction of the amidoxime IId with the benzyl compound IIIa is normally carried out at from 0° C. to 130° C., preferably 10° C. to 60° C., in an inert organic solvent in the presence of a base [cf. literature: Heterocycles 36 (1993), 1027 et seq.].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably tetrahydrofuran, acetonitrile and dimethylformamide. Mixtures of these may also be used.

Bases which are generally suitable are inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal hydrides and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride, alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, and furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. The following are especially preferred: sodium methoxide, potassium carbonate and sodium hydride.

In general, the bases are used in equimolar amounts or in an excess.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ an excess of IId based on IIIa.

The amidoximes IId required for the preparation of the compounds I which are not yet known from the literature [DE-A 44 42 732; Gazz. Chim. Ital. 55 (1925), 327] can be prepared in accordance with the literature cited.

The diazotization and halogenation of V to give I is normally carried at from −20° C. to 50° C., preferably 0° C. to 20° C., in water or in an aqueous inert organic solvent [cf. lit. J. Org. Chem. 45 (1980), 4144 et seq.; Chem. Ber. 26 (1893), 1567 et seq.].

Halogenating agents used in this reaction are hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, in particular hydrogen chloride.

In general, the halogenating agents are used in an excess or, if appropriate, as the solvent.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably are, besides water, mixtures of dioxane and water and/or tetrahydrofuran and water.

The reaction mixtures are worked up in the customary manner, for example by mixing with water, phase separation and, if appropriate, chromatographic purification of the crude products. In some cases, the intermediates and end products are obtained in the form of colorless or pale brown viscous oils, which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they can also be purified by recrystallization or digestion.

Due to the C═C and C═N double bonds, the compounds I can be obtained from their preparation in the form of E/Z isomer mixtures, it being possible for these mixtures to be separated into the pure isomers in the customary manner, for example by crystallization or chromatography.

However, if the synthesis yields isomer mixtures, separation is generally not absolutely necessary since in some cases the individual isomers can be converted into each other during formulation for use or upon use (for example when exposed to light, acids or bases). Similar conversions can also take place after use, for example in the case of the treatment of plants in the treated plants or in the harmful fungus or the animal pests to be controlled.

As regards the C═X double bond, the E isomers of the compounds I are preferred with a view to their activity (configuration based on the OCH₃ or CH₃ group relative to the COYCH₃ group).

As regards the CR²═NOR³ double bond, the cis isomers of the compounds I are generally preferred with a view to their activity (configuration based on the radical R² relative to the OR³ group).

In the definitions of the symbols given in the above formulae, collective terms were used which generally represent the following substituents:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4 or 6 carbon atoms, eg. C₁-C₆-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

Haloalkyl: straight-chain or branched alkyl groups having 1 to 4 carbon atoms (as mentioned above), it being possible for the hydrogen atoms in these groups to be partially or fully replaced by halogen atoms as mentioned above, eg. C₁-C₂-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorfluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

Alkoxy: straight-chain or branched alkyl groups having 1 to 3 or 4 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (—O—);

Haloalkoxy: straight-chain or branched haloalkyl groups having 1 to 4 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (—O—);

Alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6 carbon atoms and a double bond in any position, eg. ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

Alkynyl: straight-chain or branched hydrocarbon groups having 2 to 6 carbon atoms and a triple bond in any position, eg. ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

Cycloalkyl: monocyclic, saturated hydrocarbon groups having 3 to 6 or 5 to 6 carbon ring members, eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

Aryl: a mono- to trinuclear aromatic ring system containing 6 to 14 carbon ring members, eg. phenyl, naphthyl and anthracenyl.

The term “partially or fully halogenated” is intended to express that in groups characterized thus some or all of the hydrogen atoms of the hydrocarbon radicals can be replaced by halogen atoms as mentioned above, especially fluorine, chlorine or bromine, in particular fluorine or chlorine.

Preferred with a view to their biological activity are compounds I where Y is oxygen and X is NOCH₃, CHOCH₃ or CHCH₃.

Equally preferred are compounds I where Y is NH and X is NOCH₃.

Additionally preferred compounds I are those where R¹ is chlorine or bromine, in particular chlorine.

Furthermore, preferred compounds I are those where R² is one of the following groups:

C₂-C₆-alkyl which can be partially or fully halogenated and/or can have attached to it one or two of the following radicals: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and phenyl, it being possible for the phenyl, in turn, to be partially or fully halogenated and/or to have attached to it one to three of the following groups: cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

phenyl or benzyl which can be partially or fully halogenated in the aryl moiety and/or can have attached to it one to three of the following radicals: cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

In particular, preferred compounds I are those where R² is one of the following groups:

C₂-C₆-alkyl which can be partially or fully halogenated and/or can have attached to it one or two C₁-C₄-alkoxy radicals;

phenyl or benzyl, which can be partially or fully halogenated in the aryl moiety and/or can have attached to it one to three of the following radicals: cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

Furthermore preferred compounds I are those where R³ is one of the following groups:

C₁-C₆-alkyl, C₁-C₃-alkoxy-C₁-C₂-alkyl, C₃-C₆-alkenyl and C₃-C₆-alkynyl, it being possible for these groups to be partially or fully halogenated.

In particular, preferred compounds I are those where R³ is one of the following groups:

C₁-C₆-alkyl, C₁-C₃-alkoxy-C₁-C₂-alkyl, C₃-C₆-alkenyl and C₃-C₆-alkynyl.

Especially preferred are, in particular, compounds I where R³ is C₁-C₃-alkyl, C₁-C₃-alkoxyethyl, C₃-C₄-alkenyl or C₃-C₄-alkynyl.

Compounds I which are preferred with a view to the biological activity are, in particular, those where the substituents have the following meanings:

X is NOCH₃, CHOCH₃ or CHCH₃;

Y is O or NH;

R¹ is chlorine or bromine;

R² is

C₂-C₆-alkyl;

phenyl or benzyl which can be partially or fully halogenated in the phenyl moiety and/or can have attached to it one to three of the following radicals: cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

R³ is C₁-C₆-alkyl, C₃-C₆-alkenyl and C₃-C₆-alkynyl, it being possible for these groups to be partially halogenated.

Especially preferred with a view to their biological activity are the compounds I compiled in the Tables which follow. In addition, the groups mentioned in the Tables for a substituent are, on their own and independently of the combination in which they are mentioned, an especially preferred embodiment of the substituent in question.

TABLE 1

Compounds of the formula I.A where R¹ is chlorine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 2

Compounds of the formula I.B where R¹ is chlorine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 3

Compounds of the formula I.C where R¹ is chlorine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 4

Compounds of the formula I.D where R¹ is chlorine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 5

Compounds of the formula I.A where R¹ is fluorine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 6

Compounds of the formula I.B where R¹ is fluorine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 7

Compounds of the formula I.C where R¹ is fluorine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 8

Compounds of the formula I.D where R¹ is fluorine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 9

Compounds of the formula I.A where R¹ is bromine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 10

Compounds of the formula I.B where R¹ is bromine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 11

Compounds of the formula I.C where R¹ is bromine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 12

Compounds of the formula I.D where R¹ is bromine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 13

Compounds of the formula I.A where R¹ is iodine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 14

Compounds of the formula I.B where R¹ is iodine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 15

Compounds of the formula I.C where R¹ is iodine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 16

Compounds of the formula I.D where R¹ is iodine, R³ is methyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 17

Compounds of the formula I.A where R¹ is chlorine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 18

Compounds of the formula I.B where R¹ is chlorine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 19

Compounds of the formula I.C where R¹ is chlorine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 20

Compounds of the formula I.D where R¹ is chlorine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 21

Compounds of the formula I.A where R¹ is fluorine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 22

Compounds of the formula I.B where R¹ is fluorine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 23

Compounds of the formula I.C where R¹ is fluorine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 24

Compounds of the formula I.D where R¹ is fluorine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 25

Compounds of the formula I.A where R¹ is bromine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 26

Compounds of the formula I.B where R¹ is bromine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 27

Compounds of the formula I.C where R¹ is bromine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 28

Compounds of the formula I.D where R¹ is bromine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 29

Compounds of the formula I.A where R¹ is iodine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 30

Compounds of the formula I.B where R¹ is iodine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 31

Compounds of the formula I.C where R¹ is iodine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 32

Compounds of the formula I.D where R¹ is iodine, R³ is ethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 33

Compounds of the formula I.A where R¹ is chlorine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 34

Compounds of the formula I.B where R¹ is chlorine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 35

Compounds of the formula I.C where R¹ is chlorine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 36

Compounds of the formula I.D where R¹ is chlorine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 37

Compounds of the formula I.A where R¹ is fluorine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 38

Compounds of the formula I.B where R¹ is fluorine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 39

Compounds of the formula I.C where R¹ is fluorine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 40

Compounds of the formula I.D where R¹ is fluorine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 41

Compounds of the formula I.A where R¹ is bromine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 42

Compounds of the formula I.B where R¹ is bromine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 43

Compounds of the formula I.C where R¹ is bromine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 44

Compounds of the formula I.D where R¹ is bromine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 45

Compounds of the formula I.A where R¹ is iodine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 46

Compounds of the formula I.B where R¹ is iodine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 47

Compounds of the formula I.C where R¹ is iodine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 48

Compounds of the formula I.D where R¹ is iodine, R³ is propyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 49

Compounds of the formula I.A where R¹ is chlorine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 50

Compounds of the formula I.B where R¹ is chlorine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 51

Compounds of the formula I.C where R¹ is chlorine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 52

Compounds of the formula I.D where R¹ is chlorine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 53

Compounds of the formula I.A where R¹ is fluorine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 54

Compounds of the formula I.B where R¹ is fluorine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 55

Compounds of the formula I.C where R¹ is fluorine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 56

Compounds of the formula I.D where R¹ is fluorine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 57

Compounds of the formula I.A where R¹ is bromine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 58

Compounds of the formula I.B where R¹ is bromine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 59

Compounds of the formula I.C where R¹ is bromine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 60

Compounds of the formula I.D where R¹ is bromine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 61

Compounds of the formula I.A where R¹ is iodine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 62

Compounds of the formula I.B where R¹ is iodine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 63

Compounds of the formula I.C where R¹ is iodine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 64

Compounds of the formula I.D where R¹ is iodine, R³ is isopropyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 65

Compounds of the formula I.A where R¹ is chlorine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 66

Compounds of the formula I.B where R¹ is chlorine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 67

Compounds of the formula I.C where R¹ is chlorine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 68

Compounds of the formula I.D where R¹ is chlorine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 69

Compounds of the formula I.A where R¹ is fluorine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 70

Compounds of the formula I.B where R¹ is fluorine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 71

Compounds of the formula I.C where R¹ is fluorine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 72

Compounds of the formula I.D where R¹ is fluorine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 73

Compounds of the formula I.A where R¹ is bromine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 74

Compounds of the formula I.B where R¹ is bromine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 75

Compounds of the formula I.C where R¹ is bromine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 76

Compounds of the formula I.D where R¹ is bromine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 77

Compounds of the formula I.A where R¹ is iodine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 78

Compounds of the formula I.B where R¹ is iodine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 79

Compounds of the formula I.C where R¹ is iodine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 80

Compounds of the formula I.D where R¹ is iodine, R³ is 2-methoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 81

Compounds of the formula I.A where R¹ is chlorine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 82

Compounds of the formula I.B where R¹ is chlorine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 83

Compounds of the formula I.C where R¹ is chlorine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 84

Compounds of the formula I.D where R¹ is chlorine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 85

Compounds of the formula I.A where R¹ is fluorine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 86

Compounds of the formula I.B where R¹ is fluorine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 87

Compounds of the formula I.C where R¹ is fluorine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 88

Compounds of the formula I.D where R¹ is fluorine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 89

Compounds of the formula I.A where R¹ is bromine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 90

Compounds of the formula I.B where R¹ is bromine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 91

Compounds of the formula I.C where R¹ is bromine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 92

Compounds of the formula I.D where R¹ is bromine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 93

Compounds of the formula I.A where R¹ is iodine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 94

Compounds of the formula I.B where R¹ is iodine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 95

Compounds of the formula I.C where R¹ is iodine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 96

Compounds of the formula I.D where R¹ is iodine, R³ is 2-ethoxyethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 97

Compounds of the formula I.A where R¹ is chlorine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 98

Compounds of the formula I.B where R¹ is chlorine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 99

Compounds of the formula I.C where R¹ is chlorine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 100

Compounds of the formula I.D where R¹ is chlorine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 101

Compounds of the formula I.A where R¹ is fluorine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 102

Compounds of the formula I.B where R¹ is fluorine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 103

Compounds of the formula I.C where R¹ is fluorine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 104

Compounds of the formula I.D where R¹ is fluorine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 105

Compounds of the formula I.A where R¹ is bromine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 106

Compounds of the formula I.B where R¹ is bromine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 107

Compounds of the formula I.C where R¹ is bromine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 108

Compounds of the formula I.D where R¹ is bromine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 109

Compounds of the formula I.A where R¹ is iodine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 110

Compounds of the formula I.B where R¹ is iodine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 111

Compounds of the formula I.C where R¹ is iodine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 112

Compounds of the formula I.D where R¹ is iodine, R³ is cyclopropylmethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 113

Compounds of the formula I.A where R¹ is chlorine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 114

Compounds of the formula I.B where R¹ is chlorine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 115

Compounds of the formula I.C where R¹ is chlorine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 116

Compounds of the formula I.D where R¹ is chlorine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 117

Compounds of the formula I.A where R¹ is fluorine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 118

Compounds of the formula I.B where R¹ is fluorine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 119

Compounds of the formula I.C where R¹ is fluorine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 120

Compounds of the formula I.D where R¹ is fluorine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 121

Compounds of the formula I.A where R¹ is bromine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 122

Compounds of the formula I.B where R¹ is bromine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 123

Compounds of the formula I.C where R¹ is bromine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 124

Compounds of the formula I.D where R¹ is bromine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 125

Compounds of the formula I.A where R¹ is iodine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 126

Compounds of the formula I.B where R¹ is iodine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 127

Compounds of the formula I.C where R¹ is iodine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 128

Compounds of the formula I.D where R¹ is iodine, R³ is allyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 129

Compounds of the formula I.A where R¹ is chlorine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 130

Compounds of the formula I.B where R¹ is chlorine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 131

Compounds of the formula I.C where R¹ is chlorine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 132

Compounds of the formula I.D where R¹ is chlorine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 133

Compounds of the formula I.A where R¹ is fluorine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 134

Compounds of the formula I.B where R¹ is fluorine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 135

Compounds of the formula I.C where R¹ is fluorine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 136

Compounds of the formula I.D where R¹ is fluorine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 137

Compounds of the formula I.A where R¹ is bromine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 138

Compounds of the formula I.B where R¹ is bromine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 139

Compounds of the formula I.C where R¹ is bromine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 140

Compounds of the formula I.D where R¹ is bromine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 141

Compounds of the formula I.A where R¹ is iodine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 142

Compounds of the formula I.B where R¹ is iodine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 143

Compounds of the formula I.C where R¹ is iodine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 144

Compounds of the formula I.D where R¹ is iodine, R³ is trans-3-chloroallyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 145

Compounds of the formula I.A where R¹ is chlorine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 146

Compounds of the formula I.B where R¹ is chlorine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 147

Compounds of the formula I.C where R¹ is chlorine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 148

Compounds of the formula I.D where R¹ is chlorine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 149

Compounds of the formula I.A where R¹ is fluorine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 150

Compounds of the formula I.B where R¹ is fluorine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 151

Compounds of the formula I.C where R¹ is fluorine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 152

Compounds of the formula I.D where R¹ is fluorine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 153

Compounds of the formula I.A where R¹ is bromine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 154

Compounds of the formula I.B where R¹ is bromine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 155

Compounds of the formula I.C where R¹ is bromine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 156

Compounds of the formula I.D where R¹ is bromine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 157

Compounds of the formula I.A where R¹ is iodine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 158

Compounds of the formula I.B where R¹ is iodine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 159

Compounds of the formula I.C where R¹ is iodine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 160

Compounds of the formula I.D where R¹ is iodine, R³ is trans-butenyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 161

Compounds of the formula I.A where R¹ is chlorine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 162

Compounds of the formula I.B where R¹ is chlorine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 163

Compounds of the formula I.C where R¹ is chlorine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 164

Compounds of the formula I.D where R¹ is chlorine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 165

Compounds of the formula I.A where R¹ is fluorine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 166

Compounds of the formula I.B where R¹ is fluorine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 167

Compounds of the formula I.C where R¹ is fluorine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 168

Compounds of the formula I.D where R¹ is fluorine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 169

Compounds of the formula I.A where R¹ is bromine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 170

Compounds of the formula I.B where R¹ is bromine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 171

Compounds of the formula I.C where R¹ is bromine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 172

Compounds of the formula I.D where R¹ is bromine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 173

Compounds of the formula I.A where R¹ is iodine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 174

Compounds of the formula I.B where R¹ is iodine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 175

Compounds of the formula I.C where R¹ is iodine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 176

Compounds of the formula I.D where R¹ is iodine, R³ is propargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 177

Compounds of the formula I.A where R¹ is chlorine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 178

Compounds of the formula I.B where R¹ is chlorine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 179

Compounds of the formula I.C where R¹ is chlorine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 180

Compounds of the formula I.D where R¹ is chlorine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 181

Compounds of the formula I.A where R¹ is fluorine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 182

Compounds of the formula I.B where R¹ is fluorine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 183

Compounds of the formula I.C where R¹ is fluorine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 184

Compounds of the formula I.D where R¹ is fluorine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 185

Compounds of the formula I.A where R¹ is bromine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 186

Compounds of the formula I.B where R¹ is bromine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 187

Compounds of the formula I.C where R¹ is bromine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 188

Compounds of the formula I.D where R¹ is bromine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 189

Compounds of the formula I.A where R¹ is iodine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 190

Compounds of the formula I.B where R¹ is iodine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 191

Compounds of the formula I.C where R¹ is iodine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 192

Compounds of the formula I.D where R¹ is iodine, R³ is 3-bromopropargyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 193

Compounds of the formula I.A where R¹ is chlorine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table A

TABLE 194

Compounds of the formula I.B where R¹ is chlorine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table A

TABLE 195

Compounds of the formula I.C where R¹ is chlorine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table A

TABLE 196

Compounds of the formula I.D where R¹ is chlorine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table A

TABLE 197

Compounds of the formula I.A where R¹ is fluorine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table B

TABLE 198

Compounds of the formula I.B where R¹ is fluorine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table B

TABLE 199

Compounds of the formula I.C where R¹ is fluorine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table B

TABLE 200

Compounds of the formula I.D where R¹ is fluorine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table B

TABLE 201

Compounds of the formula I.A where R¹ is bromine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table A

TABLE 202

Compounds of the formula I.B where R¹ is bromine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table A

TABLE 203

Compounds of the formula I.C where R¹ is bromine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table A

TABLE 204

Compounds of the formula I.D where R¹ is bromine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table A

TABLE 205

Compounds of the formula I.A where R¹ is iodine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table B

TABLE 206

Compounds of the formula I.B where R¹ is iodine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table B

TABLE 207

Compounds of the formula I.C where R¹ is iodine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table B

TABLE 208

Compounds of the formula I.D where R¹ is iodine, R³ is but-3-yn-1-yl and the radical R² for a given compound corresponds to a group of Table B

TABLE 209

Compounds of the formula I.A where R¹ is chlorine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 210

Compounds of the formula I.B where R¹ is chlorine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 211

Compounds of the formula I.C where R¹ is chlorine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 212

Compounds of the formula I.D where R¹ is chlorine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 213

Compounds of the formula I.A where R¹ is fluorine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 214

Compounds of the formula I.B where R¹ is fluorine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 215

Compounds of the formula I.C where R¹ is fluorine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 216

Compounds of the formula I.D where R¹ is fluorine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 217

Compounds of the formula I.A where R¹ is bromine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 218

Compounds of the formula I.B where R¹ is bromine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 219

Compounds of the formula I.C where R¹ is bromine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 220

Compounds of the formula I.D where R¹ is bromine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 221

Compounds of the formula I.A where R¹ is iodine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 222

Compounds of the formula I.B where R¹ is iodine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 223

Compounds of the formula I.C where R¹ is iodine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 224

Compounds of the formula I.D where R¹ is iodine, R³ is fluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 225

Compounds of the formula I.A where R¹ is chlorine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 226

Compounds of the formula I.B where R¹ is chlorine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 227

Compounds of the formula I.C where R¹ is chlorine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 228

Compounds of the formula I.D where R¹ is chlorine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 229

Compounds of the formula I.A where R¹ is fluorine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 230

Compounds of the formula I.B where R¹ is fluorine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 231

Compounds of the formula I.C where R¹ is fluorine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 232

Compounds of the formula I.D where R¹ is fluorine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 233

Compounds of the formula I.A where R¹ is bromine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 234

Compounds of the formula I.B where R¹ is bromine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 235

Compounds of the formula I.C where R¹ is bromine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 236

Compounds of the formula I.D where R¹ is bromine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 237

Compounds of the formula I.A where R¹ is iodine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 238

Compounds of the formula I.B where R¹ is iodine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 239

Compounds of the formula I.C where R¹ is iodine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 240

Compounds of the formula I.D where R¹ is iodine, R³ is difluoromethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 241

Compounds of the formula I.A where R¹ is chlorine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 242

Compounds of the formula I.B where R¹ is chlorine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 243

Compounds of the formula I.C where R¹ is chlorine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 244

Compounds of the formula I.D where R¹ is chlorine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 245

Compounds of the formula I.A where R¹ is fluorine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 246

Compounds of the formula I.B where R¹ is fluorine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 247

Compounds of the formula I.C where R¹ is fluorine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 248

Compounds of the formula I.D where R¹ is fluorine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 249

Compounds of the formula I.A where R¹ is bromine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 250

Compounds of the formula I.B where R¹ is bromine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 251

Compounds of the formula I.C where R¹ is bromine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 252

Compounds of the formula I.D where R¹ is bromine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table A

TABLE 253

Compounds of the formula I.A where R¹ is iodine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 254

Compounds of the formula I.B where R¹ is iodine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 255

Compounds of the formula I.C where R¹ is iodine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE 256

Compounds of the formula I.D where R¹ is iodine, R³ is 2,2,2-trifluoroethyl and the radical R² for a given compound corresponds to a group of Table B

TABLE A No. R² A.1 CH₂CH₃ A.2 CH₂CH₂—CN A.3 CH₂CH₂—O—CH₃ A.4 CH₂CH₂—O—CH₂CH₃ A.5 CH₂CH₂CH₃ A.6 CH(CH₃)₂ A.7 CH₂CH₂CH₂CH₃ A.8 CH(CH₃)CH₂CH₃ A.9 CH₂CH(CH₃)₂ A.10 CH═CH₂ A.11 CH═CH-CH₃ (E) A.12 CH═CH—[C₆H₅] (E) A.13 CH═CH—[2-CN—C₆H₄] (E) A.14 CH═CH—[3-CN—C₆H₄] (E) A.15 CH═CH—[4-CN—C₆H₄] (E) A.16 CH═CH—[2-F—C₆H₄] (E) A.17 CH═CH—[3-F—C₆H₄] (E) A.18 CH═CH—[4-F—C₆H₄] (E) A.19 CH═CH—[2,4-F₂—C₆H₃] (E) A.20 CH═CH—[3,4-F₂—C₆H₃] (E) A.21 CH═CH—[2,4,5-F₃—C₆H₂] (E) A.22 CH═CH—[2,4,6-F₃—C₆H₂] (E) A.23 CH═CH—[2-Cl—C₆H₄] (E) A.24 CH═CH—(3-Cl—C₆H₄] (E) A.25 CH═CH—[4-Cl—C₆H₄] (E) A.26 CH═CH—[2,4-Cl₂—C₆H₃] (E) A.27 CH═CH—[3,4-Cl₂—C₆H₃] (E) A.28 CH═CH—[2,4,5-Cl₃—C₆H₂] (E) A.29 CH═CH—[2,4,6-Cl₃—C₆H₂] (E) A.30 CH═CH—[2-CH₃—C₆H₄] (E) A.31 CH═CH—[3-CH₃—C₆H₄] (E) A.32 CH═CH—[4-CH₃—C₆H₄] (E) A.33 CH═CH—[2-F, 4-CH₃—C₆H₃] (E) A.34 CH═CH—[2-CH₃, 4-F—C₆H₃] (E) A.35 CH═CH—[3-F, 4-CH₃—C₆H₃] (E) A.36 CH═CH—[3-CH₃, 4-F—C₆H₃] (E) A.37 CH═CH—[2-Cl, 4-CH₃—C₆H₃] (E) A.38 CH═CH—[2-CH₃, 4-Cl—C₆H₃] (E) A.39 CH═CH—[3-Cl, 4-CH₃—C₆H₃] (E) A.40 CH═CH—[3-CH₃, 4-Cl—C₆H₃] (E) A.41 CH═CH—[2,4-(CH₃)₂—C₆H₃] (E) A.42 CH═CH—[3,4-(CH₃)₂—C₆H₃] (E) A.43 CH═CH—[2,4,5-(CH₃)₃—C₆H₂] (E) A.44 CH═CH—[2,4,6-(CH₃)₃—C₆H₂] (E) A.45 CH═CH—[2-CF₃—C₆H₄] (E) A.46 CH═CH—[3-CF₃—C₆H₄] (E) A.47 CH═CH—[4-CF₃—C₆H₄] (E) A.48 CH═CH—[2-F, 4-CF₃—C₆H₃] (E) A.49 CH═CH—[2-CF₃, 4-F—C₆H₃] (E) A.50 CH═CH—[3-F, 4-CF₃—C₆H₃] (E) A.51 CH═CH—[3-CF₃, 4-F—C₆H₃] (E) A.52 CH═CH—[2-Cl, 4-CF₃—C₆H₃] (E) A.53 CH═CH—[2-CF₃, 4-Cl—C₆H₃] (E) A.54 CH═CH—[3-Cl, 4-CF₃—C₆H₃] (E) A.55 CH═CH—[3-CF₃, 4-Cl—C₆H₃] (E) A.56 CH═CH—[2,4-(CF₃)₂—C₆H₃] (E) A.57 CH═CH—[3,4-(CF₃)₂—C₆H₃] (E) A.58 CH═CH—[2,4,5-(CF₃)₃—C₆H₂] (E) A.59 CH═CH—[2,4,6-(CF₃)₃—C₆H₂] (E) A.60 CH═CH—[2-OCH₃—C₆H₄] (E) A.61 CH═CH—[3-OCH₃—C₆H₄] (E) A.62 CH═CH—[4-OCH₃—C₆H₄] (E) A.63 CH═CH—[2-F, 4-OCH₃—C₆H₃] (E) A.64 CH═CH—[2-OCH₃, 4-F—C₆H₃] (E) A.65 CH═CH—[3-F, 4-OCH₃—C₆H₃] (E) A.66 CH═CH—[3-OCH₃, 4-F—C₆H₃] (E) A.67 CH═CH—[2-Cl, 4-OCH₃—C₆H₃] (E) A.68 CH═CH—[2-OCH₃, 4-Cl—C₆H₃] (E) A.69 CH═CH—[3-Cl, 4-OCH₃—C₆H₃] (E) A.70 CH═CH—[3-OCH₃, 4-Cl—C₆H₃] (E) A.71 CH═CH—[2,4-(OCH₃)₂—C₆H₃] (E) A.72 CH═CH—[3,4-(OCH₃)₂—C₆H₃] (E) A.73 CH═CH—[2,4,5-(OCH₃)₃—C₆H₂] (E) A.74 CH═CH—[2,4,6-(OCH₃)₃—C₆H₂] (E) A.75 CH═CH—[2-OCHF₂—C₆H₄] (E) A.76 CH═CH—[3-OCHF₂—C₆H₄] (E) A.77 CH═CH—[4-OCHF₂—C₆H₄] (E) A.78 CH═CH—[2-F, 4-OCHF₂—C₆H₃] (E) A.79 CH═CH—[2-OCHF₂, 4-F—C₆H₃] (E) A.80 CH═CH—[3-F, 4-OCHF₂—C₆H₃] (E) A.81 CH═CH—[3-OCHF₂, 4-F—C₆H₃] (E) A.82 CH═CH—[2-Cl, 4-OCHF₂—C₆H₃] (E) A.83 CH═CH—[2-OCHF₂, 4-Cl—C₆H₃] (E) A.84 CH═CH—[3-Cl, 4-OCHF₂—C₆H₃] (E) A.85 CH═CH—[3-OCHF₂, 4-Cl—C₆H₃] (E) A.86 CH═CH—[2,4-(OCHF₂)₂—C₆H₃] (E) A.87 CH═CH—[3,4-(OCHF₂)₂—C₆H₃] (E) A.88 CH═CH—[2,4,5-(OCHF₂)₃—C₆H₂] (E) A.89 CH═CH—[2,4,6-(OCHF₂)₃—C₆H₂] (E) A.90 CH₂CH═CH₂ A.91 CH₂CH═CH—Cl (E) A.92 CH₂CH═CH—Br (E) A.93 CH₂CH═CH—CH₃ (E) A.94 C≡CH A.95 C≡C—Cl A.96 C≡C—Br A.97 C≡C—CH₃ A.98 C≡C—C₆H₅ A.99 C≡C—[2-Cl—C₆H₄] A.100 C≡C—[4-Cl—C₆H₄] A.101 C≡C—[2,4-Cl₂—C₆H₃] A.102 C≡C—[2-CH₃—C₆H₄] A.103 C≡C—[4-CH₃—C₆H₄] A.104 C≡C—[2,4-(CH₃)₂—C₆H₃] A.105 C≡C—[2-Cl, 4-CH₃—C₆H₃] A.106 C≡C—[2-CH₃, 4-Cl—C₆H₃] A.107 C≡C—[3-CF₃—C₆H₄] A.108 C≡C—[3-Cl, 5-CF₃—C₆H₃] A.109 C≡C—[2-OCH₃—C₆H₄] A.110 C≡C—[4-OCH₃—C₆H₄] A.111 C≡C—[2,4-(OCH₃)₂—C₆H₃] A.112 C≡C—[2-Cl, 4-OCH₃—C₆H₃] A.113 C≡C—[2-OCH₃, 4-Cl—C₆H₃] A.114 C≡C—[3-OCHF₂—C₆H₄] A.115 C≡C—[3-Cl, 5-OCHF₂—C₆H₃] A.116 cyclopentyl A.117 1-CH₃-cyclopentyl A.118 2-CH₃-cyclopentyl A.119 3-CH₃-cyclopentyl A.120 2,3-(CH₃)₂-cyclopentyl A.121 1-Cl-cyclopentyl A.122 2-Cl-cyclopentyl A.123 3-Cl-cyclopentyl A.124 2-CH₃, 3-Cl-cyclopentyl A.125 2,3-Cl₂-cyclopentyl A.126 cyclohexyl A.127 1-CH₃-cyclohexyl A.128 2-CH₃-cyclohexyl A.129 3-CH₃-cyclohexyl A.130 2,3-(CH₃)₂-cyclohexyl A.131 3,3-(CH₃)₂-cyclohexyl A.132 1-Cl-cyclohexyl A.133 2-Cl-cyclohexyl A.134 3-Cl-cyclohexyl A.135 2-CH₃, 3-Cl-cyclohexyl A.136 2,3-Cl₂—cyclohexyl A.137 C₆H₅ A.138 2-CN—C₆H₄ A.139 3-CN—C₆H₄ A.140 4-CN—C₆H₄ A.141 2-F—C₆H₄ A.142 3-F—C₆H₄ A.143 4-F—C₆H₄ A.144 2,4-F₂—C₆H₃ A.145 3,4-F₂—C₆H₃ A.146 2,4,5-F₃—C₆H₂ A.147 2,4,6-F₃—C₆H₂ A.148 2-Cl—C₆H₄ A.149 3-Cl—C₆H₄ A.150 4-Cl—C₆H₄ A.151 2,4-Cl₂—C₆H₃ A.152 3,4-Cl₂—C₆H₃ A.153 2,4,5-Cl₃—C₆H₂ A.154 2,4,6-Cl₃—C₆H₂ A.155 2-CH₃—C₆H₄ A.156 3-CH₃—C₆H₄ A.157 4-CH₃—C₆H₄ A.158 2-F, 4-CH₃—C₆H₃ A.159 2-CH₃, 4-F—C₆H₃ A.160 3-F, 4-CH₃—C₆H₃ A.161 3-CH₃, 4-F—C₆H₃ A.162 2-Cl, 4-CH₃—C₆H₃ A.163 2-CH₃, 4-Cl—C₆H₃ A.164 3-Cl, 4-CH₃—C₆H₃ A.165 3-CH₃, 4-Cl—C₆H₃ A.166 2,4-(CH₃)₂—C₆H₃ A.167 3,4-(CH₃)₂—C₆H₃ A.168 2,4,5-(CH₃)₃—C₆H₂ A.169 2,4,6-(CH₃)₃—C₆H₂ A.170 2-CF₃—C₆H₄ A.171 3-CF₃—C₆H₄ A.172 4-CF₃—C₆H₄ A.173 2-F, 4-CF₃—C₆H₃ A.174 2-CF₃, 4-F—C₆H₃ A.175 3-F, 4-CF₃—C₆H₃ A.176 3-CF₃, 4-F—C₆H₃ A.177 2-Cl, 4-CF₃—C₆H₃ A.178 2-CF₃, 4-Cl—C₆H₃ A.179 3-Cl, 4-CF₃—C₆H₃ A.180 3-CF₃, 4-Cl—C₆H₃ A.181 2,4-(CF₃)₂—C₆H₃ A.182 3,4-(CF₃)₂—C₆H₃ A.183 2,4,5-(CF₃)₃—C₆H₂ A.184 2,4,6-(CF₃)₃—C₆H₂ A.185 2-OCH₃—C₆H₄ A.186 3-OCH₃—C₆H₄ A.187 4-OCH₃—C₆H₄ A.188 2-F, 4-OCH₃—C₆H₃ A.189 2-OCH₃, 4-F—C₆H₃ A.190 3-F, 4-OCH₃—C₆H₃ A.191 3-OCH₃, 4-F—C₆H₃ A.192 2-Cl, 4-OCH₃—C₆H₃ A.193 2-OCH₃, 4-Cl—C₆H₃ A.194 3-Cl, 4-OCH₃—C₆H₃ A.195 3-OCH₃, 4-Cl—C₆H₃ A.196 2,4-(OCH₃)₂—C₆H₃ A.197 3,4-(OCH₃)₂—C₆H₃ A.198 2,4,5-(OCH₃)₃—C₆H₂ A.199 2,4,6-(OCH₃)₃—C₆H₂ A.200 2-OCHF₂—C₆H₄ A.201 3-OCHF₂—C₆H₄ A.202 4-OCHF₂—C₆H₄ A.203 2-F, 4-OCHF₂—C₆H₃ A.204 2-OCHF₂, 4-F—C₆H₃ A.205 3-F, 4-OCHF₂—C₆H₃ A.206 3-OCHF₂, 4-F—C₆H₃ A.207 2-Cl, 4-OCHF₂—C₆H₃ A.208 2-OCHF₂, 4-Cl—C₆H₃ A.209 3-Cl, 4-OCHF₂—C₆H₃ A.210 3-OCHF₂, 4-Cl—C₆H₃ A.211 2,4-(OCHF₂)₂—C₆H₃ A.212 3,4-(OCHF₂)₂—C₆H₃ A.213 2,4,5-(OCHF₂)₃—C₆H₂ A.214 2,4,6-(OCHF₂)₃—C₆H₂ A.215 CH₂—C₆H₅ A.216 CH₂—[2-CN—C₆H₄] A.217 CH₂—[3-CN—C₆H₄] A.218 CH₂—[4-CN—C₆H₄] A.219 CH₂—[2-F—C₆H₄] A.220 CH₂—[3-F—C₆H₄] A.221 CH₂—[4-F—C₆H₄] A.222 CH₂—[2,4-F₂—C₆H₃] A.223 CH₂—[3,4-F₂—C₆H₃] A.224 CH₂—[2,4,5-F₃—C₆H₂] A.225 CH₂—[2,4,6-F₃—C₆H₂] A.226 CH₂—[2-Cl—C₆H₄] A.227 CH₂—[3-Cl—C₆H₄] A.228 CH₂—[4-Cl—C₆H₄] A.229 CH₂—[2,4-Cl₂—C₆H₃] A.230 CH₂—[3,4-Cl₂—C₆H₃] A.231 CH₂—[2,4,5-Cl₃—C₆H₂] A.232 CH₂—[2,4,6-Cl₃—C₆H₂] A.233 CH₂—[2-CH₃—C₆H₄] A.234 CH₂—[3-CH₃—C₆H₄] A.235 CH₂—[4-CH₃—C₆H₄] A.236 CH₂—[2-F, 4-CH₃—C₆H₃] A.237 CH₂—[2-CH₃, 4-F—C₆H₃] A.238 CH₂—[3-F, 4-CH₃—C₆H₃] A.239 CH₂—[3-CH₃, 4-F—C₆H₃] A.240 CH₂—[2-Cl, 4-CH₃—C₆H₃] A.241 CH₂—[2-CH₃, 4-Cl—C₆H₃] A.242 CH₂—[3-Cl, 4-CH₃—C₆H₃] A.243 CH₂—[3-CH₃, 4-Cl—C₆H₃] A.244 CH₂—[2,4-(CH₃)₂—C₆H₃] A.245 CH₂—[3,4-(CH₃)₂—C₆H₃] A.246 CH₂—[2,4,5-(CH₃)₃—C₆H₂] A.247 CH₂—[2,4,6-(CH₃)₃—C₆H₂] A.248 CH₂—[2-CF₃—C₆H₄] A.249 CH₂—[3-CF₃—C₆H₄] A.250 CH₂—[4-CF₃—C₆H₄] A.251 CH₂—[2-F, 4-CF₃—C₆H₃] A.252 CH₂—[2-CF₃, 4-F—C₆H₃] A.253 CH₂—[3-F, 4-CF₃—C₆H₃] A.254 CH₂—[3-CF₃, 4-F—C₆H₃] A.255 CH₂—[2-Cl, 4-CF₃—C₆H₃] A.256 CH₂—[2-CF₃, 4-Cl—C₆H₃] A.257 CH₂—[3-Cl, 4-CF₃—C₆H₃] A.258 CH₂—[3-CF₃, 4-Cl—C₆H₃] A.259 CH₂—[2,4-(CF₃)₂—C₆H₃] A.260 CH₂—[3,4-(CF₃)₂—C₆H₃] A.261 CH₂—[2,4,5-(CF₃)₃—C₆H₂] A.262 CH₂—[2,4,6-(CF₃)₃—C₆H₂] A.263 CH₂—[2-OCH₃—C₆H₄] A.264 CH₂—[3-OCH₃—C₆H₄] A.265 CH₂—[4-OCH₃—C₆H₄] A.266 CH₂—[2-F, 4-OCH₃—C₆H₃] A.267 CH₂—[2-OCH₃, 4-F—C₆H₃] A.268 CH₂—[3-F, 4-OCH₃—C₆H₃] A.269 CH₂—[3-OCH₃, 4-F—C₆H₃] A.270 CH₂—[2-Cl, 4-OCH₃—C₆H₃] A.271 CH₂—[2-OCH₃, 4-Cl—C₆H₃] A.272 CH₂—[3-Cl, 4-OCH₃—C₆H₃] A.273 CH₂—[3-OCH₃, 4-Cl—C₆H₃] A.274 CH₂—[2,4-(OCH₃)₂—C₆H₃] A.275 CH₂—[3,4-(OCH₃)₂—C₆H₃] A.276 CH₂—[2,4,5-(OCH₃)₃—C₆H₂] A.277 CH₂—[2,4,6-(OCH₃)₃—C₆H₂] A.278 CH₂—[2-OCHF₂—C₆H₄] A.279 CH₂—[3-OCHF₂—C₆H₄] A.280 CH₂—[4-OCHF₂—C₆H₄] A.281 CH₂—[2-F, 4-OCHF₂—C₆H₃] A.282 CH₂—[2-OCHF₂, 4-F—C₆H₃] A.283 CH₂—[3-F, 4-OCHF₂—C₆H₃] A.284 CH₂—[3-OCHF₂, 4-F—C₆H₃] A.285 CH₂—[2-Cl, 4-OCHF₂—C₆H₃] A.286 CH₂—[2-OCHF₂, 4-Cl—C₆H₃] A.287 CH₂—[3-Cl, 4-OCHF₂—C₆H₃] A.288 CH₂—[3-OCHF₂, 4-Cl—C₆H₃] A.289 CH₂—[2,4-(OCHF₂)₂—C₆H₃] A.290 CH₂—[3,4-(OCHF₂)₂—C₆H₃] A.291 CH₂—[2,4,5-(OCHF₂)₃—C₆H₂] A.292 CH₂—[2,4,6-(OCHF₂)₃—C₆H₂] A.293 CH(CH₃)—C₆H₅ A.294 CH(CH₃)—[2-CN—C₆H₄] A.295 CH(CH₃)—[3-CN—C₆H₄] A.296 CH(CH₃)—[4-CN—C₆H₄] A.297 CH(CH₃)—[2-F—C₆H₄] A.298 CH(CH₃)—[3-F—C₆H₄) A.299 CH(CH₃)—[4-F—C₆H₄] A.300 CH(CH₃)—[2,4-F₂—C₆H₃] A.301 CH(CH₃)—[3,4-F₂—C₆H₃] A.302 CH(CH₃)—[2,4,5-F₃—C₆H₂] A.303 CH(CH₃)—[2,4,6-F₃—C₆H₂] A.304 CH(CH₃)—[2-Cl—C₆H₄] A.305 CH(CH₃)—[3-Cl—C₆H₄] A.306 CH(CH₃)—[4-Cl—C₆H₄] A.307 CH(CH₃)—[2,4-Cl₂—C₆H₃] A.308 CH(CH₃)—[3,4-Cl₂—C₆H₃] A.309 CH(CH₃)—[2,4,5-Cl₃—C₆H₂] A.310 CH(CH₃)—[2,4,6-Cl₃—C₆H₂] A.311 CH(CH₃)—[2-CH₃—C₆H₄] A.312 CH(CH₃)—[3-CH₃—C₆H₄] A.313 CH(CH₃)—[4-CH₃—C₆H₄] A.314 CH(CH₃)—[2-F, 4-CH₃—C₆H₃] A.315 CH(CH₃)—[2-CH₃, 4-F—C₆H₃] A.316 CH(CH₃)—[3-F, 4-CH₃—C₆H₃] A.317 CH(CH₃)—[3-CH₃, 4-F—C₆H₃] A.318 CH(CH₃)—[2-Cl, 4-CH₃—C₆H₃] A.319 CH(CH₃)—[2-CH₃, 4-Cl—C₆H₃] A.320 CH(CH₃)—[3-Cl, 4-CH₃—C₆H₃] A.321 CH(CH₃)—[3-CH₃, 4-Cl—C₆H₃] A.322 CH(CH₃)—[2,4-(CH₃)₂—C₆H₃] A.323 CH(CH₃)—[3,4-(CH₃)₂—C₆H₃] A.324 CH(CH₃)—[2,4,5-(CH₃)₃—C₆H₂] A.325 CH(CH₃)—[2,4,6-(CH₃)₃—C₆H₂] A.326 CH(CH₃)—[2-CF₃—C₆H₄] A.327 CH(CH₃)—[3-CF₃—C₆H₄] A.328 CH(CH₃)—[4-CF₃—C₆H₄] A.329 CH(CH₃)—[2-F, 4-CF₃—C₆H₃] A.330 CH(CH₃)—[2-CF₃, 4-F—C₆H₃] A.331 CH(CH₃)—[3-F, 4-CF₃—C₆H₃] A.332 CH(CH₃)—[3-CF₃, 4-F—C₆H₃] A.333 CH(CH₃)—[2-Cl, 4-CF₃—C₆H₃] A.334 CH(CH₃)—[2-CF₃, 4-Cl—C₆H₃] A.335 CH(CH₃)—[3-Cl, 4-CF₃—C₆H₃] A.336 CH(CH₃)—[3-CF₃, 4-Cl—C₆H₃] A.337 CH(CH₃)—[2,4-(CF₃)₂—C₆H₃] A.338 CH(CH₃)—[3,4-(CF₃)₂—C₆H₃] A.339 CH(CH₃)—[2,4,5-(CF₃)₃—C₆H₂] A.340 CH(CH₃)—[2,4,6-(CF₃)₃—C₆H₂] A.341 CH(CH₃)—[2-OCH₃—C₆H₄] A.342 CH(CH₃)—[3-OCH₃—C₆H₄] A.343 CH(CH₃)—[4-OCH₃—C₆H₄] A.344 CH(CH₃)—[2-F, 4-OCH₃—C₆H₃] A.345 CH(CH₃)—[2-OCH₃, 4-F—C₆H₃] A.346 CH(CH₃)—[3-F, 4-OCH₃—C₆H₃] A.347 CH(CH₃)—[3-OCH₃, 4-F—C₆H₃] A.348 CH(CH₃)—[2-Cl, 4-OCH₃—C₆H₃] A.349 CH(CH₃)—[2-OCH₃, 4-Cl—C₆H₃] A.350 CH(CH₃)—[3-Cl, 4-OCH₃—C₆H₃] A.351 CH(CH₃)—[3-OCH₃, 4-Cl—C₆H₃] A.352 CH(CH₃)—[2,4-(OCH₃)₂—C₆H₃] A.353 CH(CH₃)—[3,4-(OCH₃)₂—C₆H₃] A.354 CH(CH₃)—[2,4,5-(OCH₃)₃—C₆H₂] A.355 CH(CH₃)—[2,4,6-(OCH₃)₃—C₆H₂] A.356 CH(CH₃)—[2-OCHF₂—C₆H₄] A.357 CH(CH₃)—[3-OCHF₂—C₆H₄] A.358 CH(CH₃)—[4-OCHF₂—C₆H₄] A.359 CH(CH₃)—[2-F, 4-OCHF₂—C₆H₃] A.360 CH(CH₃)—[2-OCHF₂, 4-F—C₆H₃] A.361 CH(CH₃)—[3-F, 4-OCHF₂—C₆H₃] A.362 CH(CH₃)—[3-OCHF₂, 4-F—C₆H₃] A.363 CH(CH₃)—[2-Cl, 4-OCHF₂—C₆H₃] A.364 CH(CH₃)—[2-OCHF₂, 4-Cl—C₆H₃] A.365 CH(CH₃)—[3-Cl, 4-OCHF₂—C₆H₃] A.366 CH(CH₃)—[3-OCHF₂, 4-Cl—C₆H₃] A.367 CH(CH₃)—[2,4-(OCHF₂)₂—C₆H₃] A.368 CH(CH₃)—[3,4-(OCHF₂)₂—C₆H₃] A.369 CH(CH₃)—[2,4,5-(OCHF₂)₃—C₆H₂] A.370 CH(CH₃)—[2,4,6-(OCHF₂)₃—C₆H₂] A.371 CH₂F A.372 CHF₂ A.373 CF₃ A.374 CH₂—CN A.375 CH₂—OCH₃ A.376 CH₂—OCH₂CH₃ A.377 CH₂—OCH₂CH₂CH₃ A.378 CH₂—OCH(CH₃)₂ A.379 CH₂—OCH₂CH₂CH₂CH₃ A.380 CH₂—OCH(CH₃)CH₂CH₃ A.381 CH₂—OCH₂CH(CH₃)₂ A.382 CH₂—OC(CH₃)₃ A.383 CH₂—OCF₃ A.384 CH₂—OCH₂CF₃ A.385 CH₂CH₂—OCH₂CH₂CH₃ A.386 CH₂CH₂—OCH(CH₃)₂ A.387 CH₂CH₂—OCH₂CH₂CH₂CH₃ A.388 CH₂CH₂—OCH(CH₃)CH₂CH₃ A.389 CH₂CH₂—OCH₂CH(CH₃)₂ A.390 CH₂CH₂—OC(CH₃)₃ A.391 CH₂CH₂—OCF₃ A.392 CH₂CH₂—OCH₂CF₃ A.393 CH₂CH₂—[C₆H₅] A.394 CH₂CH₂—[2-CN—C₆H₄] A.395 CH₂CH₂—[3-CN—C₆H₄] A.396 CH₂CH₂—[4-CN—C₆H₄] A.397 CH₂CH₂—[2-F—C₆H₄] A.398 CH₂CH₂—[3-F—C₆H₄] A.399 CH₂CH₂—[4-F—C₆H₄] A.400 CH₂CH₂—[2,4-F₂—C₆H₃] A.401 CH₂CH₂—[3,4-F₂—C₆H₃] A.402 CH_(2CH) ₂—[2,4,5-F₃—C₆H₂] A.403 CH₂CH₂—[2,4,6-F₃—C₆H₂] A.404 CH₂CH₂—[2-Cl—C₆H₄] A.405 CH₂CH₂—[3-Cl—C₆H₄] A.406 CH₂CH₂—[4-Cl—C₆H₄] A.407 CH₂CH₂—[2,4-Cl₂—C₆H₃] A.408 CH₂CH₂—[3,4-Cl₂—C₆H₃] A.409 CH₂CH₂—[2,4,5-Cl₃—C₆H₂] A.410 CH₂CH₂—[2,4,6-Cl₃—C₆H₂] A.411 CH₂CH₂—[2-CH₃—C₆H₄] A.412 CH₂CH₂—[3-CH₃—C₆H₄] A.413 CH₂CH₂—[4-CH₃—C₆H₄] A.414 CH₂CH₂—[2-F, 4-CH₃—C₆H₃] A.415 CH₂CH₂—[2-CH₃, 4-F—C₆H₃] A.416 CH₂CH₂—[3-F, 4-CH₃—C₆H₃] A.417 CH₂CH₂—[3-CH₃, 4-F—C₆H₃] A.418 CH₂CH₂—[2-Cl, 4-CH₃—C₆H₃] A.419 CH₂CH₂—[2-Cl, 4-CH₃—C₆H₃] A.420 CH₂CH₂—[3-Cl, 4-CH₃—C₆H₃] A.421 CH₂CH₂—[3-CH₃, 4-Cl—C₆H₃] A.422 CH₂CH₂—[2,4-(CH₃)₂—C₆H₃] A.423 CH₂CH₂—[3,4-(CH₃)₂—C₆H₃] A.424 CH₂CH₂—[2,4,5-(CH₃)₃—C₆H₂] A.425 CH₂CH₂—[2,4,6-(CH₃)₃—C₆H₂] A.426 CH₂CH₂—[2-CF₃—C₆H₄] A.427 CH₂CH₂—[3-CF₃—C₆H₄) A.428 CH₂CH₂—[4-CF₃—C₆H₄] A.429 CH₂CH₂—[2-F, 4-CF₃—C₆H₃] A.430 CH₂CH₂—[2-CF₃, 4-F—C₆H₃] A.431 CH₂CH₂—[3-F, 4-CF₃—C₆H₃] A.432 CH₂CH₂—[3-CF₃, 4-F—C₆H₃] A.433 CH₂CH₂—[2-Cl, 4-CF₃—C₆H₃] A.434 CH₂CH₂—[2-CF₃, 4-Cl—C₆H₃) A.435 CH₂CH₂—[3-Cl, 4-CF₃—C₆H₃] A.436 CH₂CH₂—[3-CF₃, 4-Cl—C₆H₃] A.437 CH₂CH₂—[2,4-(CF₃)₂—C₆H₃] A.438 CH₂CH₂—[3,4-(CF₃)₂—C₆H₃) A.439 CH₂CH₂—[2,4,5-(CF₃)₃—C₆H₂] A.440 CH₂CH₂—[2,4,6-(CF₃)₃—C₆H₂] A.441 CH₂CH₂—[2-OCH₃—C₆H₄] A.442 CH₂CH₂—[3-OCH₃—C₆H₄] A.443 CH₂CH₂—[4-OCH₃—C₆H₄] A.444 CH₂CH₂—[2-F, 4-OCH₃—C₆H₃] A.445 CH₂CH₂—[2-OCH₃, 4-F—C₆H₃] A.446 CH₂CH₂—[3-F, 4-OCH₃—C₆H₃] A.447 CH₂CH₂—[3-OCH₃, 4-F—C₆H₃] A.448 CH₂CH₂—[2-Cl, 4-OCH₃—C₆H₃] A.449 CH₂CH₂—[2-OCH₃, 4-Cl—C₆H₃] A.450 CH₂CH₂—[3-Cl, 4-OCH₃—C₆H₃] A.451 CH₂CH₂—[3-OCH₃, 4-Cl—C₆H₃] A.452 CH₂CH₂—[2,4-(OCH₃)₂—C₆H₃] A.453 CH₂CH₂—[3,4-(OCH₃)₂—C₆H₃] A.454 CH₂CH₂—[2,4,5-(OCH₃)₃—C₆H₂] A.455 CH₂CH₂—[2,4,6-(OCH₃)₃—C₆H₂] A.456 CH₂CH₂—[2-OCHF₂—C₆H₄] A.457 CH₂CH₂—[3-OCHF₂—C₆H₄] A.458 CH₂CH₂—[4-OCHF₂—C₆H₄] A.459 CH₂CH₂—[2-F, 4-OCHF₂—C₆H₃] A.460 CH₂CH₂—[2-OCHF₂, 4-F—C₆H₃] A.461 CH₂CH₂—[3-F, 4-OCHF₂—C₆H₃] A.462 CH₂CH₂—[3-OCHF₂, 4-F—C₆H₃] A.463 CH₂CH₂—[2-Cl, 4-OCHF₂—C₆H₃] A.464 CH₂CH₂—[2-OCHF₂, 4-Cl—C₆H₃] A.465 CH₂CH₂—[3-Cl, 4-OCHF₂—C₆H₃] A.466 CH₂CH₂—[3-OCHF₂, 4-Cl—C₆H₃] A.467 CH₂CH₂—[2,4-(OCHF₂)₂—C₆H₃] A.468 CH₂CH₂—[3,4-(OCHF₂)₂—C₆H₃] A.469 CH₂CH₂—[2,4,5-(OCHF₂)₃—C₆H₂] A.470 CH₂CH₂—[2,4,6-(OCHF₂)₃—C₆H₂]) A.471 CH(CH₃)—CN A.472 CH(CH₃)—OCH₃ A.473 CH(CH₃)—OCH₂CH₃ A.474 CH(CH₃)—OCH₂CH₂CH₃ A.475 CH(CH₃)—OCH(CH₃)₂ A.476 CH(CH₃)—OCH₂CH2CH₂CH₃ A.477 CH(CH₃)—OCH(CH₃)CH₂CH₃ A.478 CH(CH₃)—OCH₂CH(CH₃)₂ A.479 CH(CH₃)—OC(CH₃)₃ A.480 CH(CH₃)—OCF₃ A.481 CH(CH₃)—OCH₂CF₃ A.482 CH₂CH₂F A.483 CH₂CHF₂ A.484 CH₂CF₃ A.485 CHFCH₃ A.486 CF₂CH₃ A.487 CHFCHF₂ A.488 CHFCF₃ A.489 CF₂CHF₂ A.490 CF₂CF₃ A.491 CF₂CHFCl A.492 CH₂CH₂CH₂—CN A.493 CH₂CH₂CH₂—OCH₃ A.494 CH₂CH₂CH₂—OCH₂CH₃ A.495 CH₂CH₂CH₂—OCH₂CH₂CH₃ A.496 CH₂CH₂CH₂—OCH(CH₃)₂ A.497 CH₂CH₂CH₂—OCF₃ A.498 CH₂CH₂CH₂—OCH₂CF₃ A.499 CH₂CH(CH₃)—CN A.500 CH₂CH(CH₃)—OCH₃ A.501 CH₂CH(CH₃)—OCH₂CH₃ A.502 CH₂CH(CH₃)—OCH₂CH₂CH₃ A.503 CH₂CH(CH₃)—OCH(CH₃)₂ A.504 CH₂CH(CH₃)—OCF₃ A.505 CH₂CH(CH₃)—OCH₂CF₃ A.506 CH(CH₂CH₃)—CN A.507 CH(CH₂CH₃)—OCH₃ A.508 CH(CH₂CH₃)—OCH₂CH₃ A.509 CH(CH₂CH₃)—OCH₂CH₂CH₃ A.510 CH(CH₂CH₃)—OCH(CH₃)₂ A.511 CH(CH₂CH₃)—OCF₃ A.512 CH(CH₂CH₃)—OCH₂CF₃ A.513 CH(CH₃)CH₂—CN A.514 CH(CH₃)CH₂—OCH₃ A.515 CH(CH₃)CH₂—OCH₂CH₃ A.516 CH(CH₃)CH₂—OCH₂CH₂CH₃ A.517 CH(CH₃)CH₂—OCH(CH₃)₂ A.518 CH(CH₃)CH₂—OCF₃ A.519 CH(CH₃)CH₂—OCH₂CF₃ A.520 CH₂CH₂CF₃ A.521 CH₂CF₃CF₃ A.522 CHFCH₂CH₃ A.523 CH(CF₃)CH₃ A.524 CH(CF₃)₂ A.525 CH₂CH₂CH₂CH₂—CN A.526 CH₂CH₂CH₂CH₂—OCH₃ A.527 CH₂CH₂CH₂CH₂—OCH₂CH₃ A.528 CH₂CH₂CH₂CH₂—OCF₃ A.529 CH(CN)—CH₂CH₂CH₃ A.530 CH(OCH₃)—CH₂CH₂CH₃ A.531 CH(OCH₂CH₃)—CH₂CH₂CH₃ A.532 CH(OCF₃)—CH₂CH₂CH₃ A.533 CH(OCH₂CF₃)—CH₂CH₂CH₃ A.534 CH(CN)—CH₂CH(CH₃)₂ A.535 CH(OCH₃)—CH₂CH(CH₃)₂ A.536 CH(OCH₂CH₃)—CH₂CH(CH₃)₂ A.537 CH(OCF₃)—CH₂CH(CH₃)₂ A.538 CH(OCH₂CF₃)—CH₂CH(CH₃)₂ A.539 CHFCH₂CH₂CH₃ A.540 C(CH₃)═CH₂ A.541 CH═CH—CH₃ (Z) A.542 C(CH₂CH₃)═CH₂ A.543 C(CH₃)═CH—CH₃ (E) A.544 C(CH₃)═CH—CH₃ (Z) A.545 C(CH₃)═C(CH₃)₂ A.546 CH(CH₃)—CH═CH₂ A.547 CH═C(CH₃)₂ A.548 CH₂—C(CH₃)═CH₂ A.549 CH(CH₃)—CH₂—CH═CH₂ A.550 CH₂—CH(CH₃)—CH═CH₂ A.551 CH₂—CCl═CH₂ A.552 CH₂—CH═CH—Cl (Z) A.553 CH₂—CCl═CH—Cl (E) A.554 CH₂—CCl═CH—Cl (Z) A.555 CH₂—CH═CCl₂ A.556 CH₂—CCl═CCl₂ A.557 CH₂—CBr═CH₂ A.558 CH₂—CH═CH—Br (Z) A.559 CH₂—CBr═CH—Br (E) A.560 CH₂—CBr═CH—Br (Z) A.561 CH₂—CH═CBr₂ A.562 CH₂—CBr═CBr₂ A.563 CH₂—CH═CH—CH₃ (Z) A.564 CH₂—C(CH₃)═CH—CH₃ (E) A.565 CH₂—C(CH₃)═CH—CH₃ (Z) A.566 CH₂—CH═C(CH₃)₂ A.567 CH₂—CH₂—CH═CH₂ A.568 CH₂—CCl═CH—CH₃ (E) A.569 CH₂—CCl═CH—CH₃ (Z) A.570 CH₂—CH═CCl—CH₃ (E) A.571 CH₂—CH═CCl—CH₃ (Z) A.572 CH₂—C(CH₃)═C(CH₃)₂ A.573 CH₂—CBr═CH—CH₃ (E) A.574 CH₂—CBr═CH—CH₃ (Z) A.575 CH₂—CH═CBr—CH₃ (E) A.576 CH₂—CH═CBr—CH₃ (Z) A.577 CH₂—CH═CH—CH₂Cl (E) A.578 CH₂—CH═CH—CH₂Cl (Z) A.579 CH₂—CH═CH—CH₂CH₃ (E) A.580 CH₂—CH═CH—CH₂CH₃ (Z) A.581 CH₂—CH═CH—CH₂Br (E) A.582 CH₂—CH═CH—CH₂Br (Z) A.583 CH₂—CCl═CCl—CH₂Cl (E) A.584 CH₂—CCl═CCl—CH₂Cl (Z) A.585 CH₂—CF═CH₂ A.586 CH₂—CH═CH—F (E) A.587 CH₂—CH═CH—F (Z) A.588 CH₂—CH═CF₂ A.589 CH₂—CF═CH—F (E) A.590 CH₂—CF═CH—F (Z) A.591 CH(CH₃)—CH═CH₂ A.592 CH(CH₃)—CCl═CH₂ A.593 CH(CH₃)—CH═CH—Cl (E) A.594 CH(CH₃)—CH═CH—Cl (Z) A.595 CH(CH₃)—CCl═CH—Cl (E) A.596 CH(CH₃)—CCl═CH—Cl (Z) A.597 CH(CH₃)—CH═CCl₂ A.598 CH(CH₃)—CCl═CCl₂ A.599 CH(CH₃)—CBr═CH₂ A.600 CH(CH₃)—CH═CH—Br (E) A.601 CH(CH₃)—CH═CH—Br (Z) A.602 CH(CH₃)—CBr═CH—Br (E) A.603 CH(CH₃)—CBr═CH—Br (Z) A.604 CH(CH₃)—CH═CBr₂ A.605 CH(CH₃)—CBr═CBr₂ A.606 CH(CH₃)—C(CH₃)═CH₂ A.607 CH(CH₃)—CH═CH—CH₃ (E) A.608 CH(CH₃)—CH═CH—CH₃ (Z) A.609 CH(CH₃)—C(CH₃)═CH—CH₃ (E) A.610 CH(CH₃)—C(CH₃)═CH—CH₃ (Z) A.611 CH(CH₃)—CH═C(CH₃)₂ A.612 CH(CH₃)—CCl═CH—CH₃ (E) A.613 CH(CH₃)—CCl═CH—CH₃ (Z) A.614 CH(CH₃)—CH═CCl—CH₃ (E) A.615 CH(CH₃)—CH═CCl—CH₃ (Z) A.616 CH(CH₃)—CBr═CH—CH₃ (E) A.617 CH(CH₃)—CBr═CH—CH₃ (Z) A.618 CH(CH₃)—CH═CBr—CH₃ (E) A.619 CH(CH₃)—CH═CBr—CH₃ (Z) A.620 CH(CH₃)—CH═CH—CH₂Cl (E) A.621 CH(CH₃)—CH═CH—CH₂Cl (Z) A.622 CH(CH₃)—CH═CH—CH₂CH₃ (E) A.623 CH(CH₃)—CH═CH—CH₂CH₃ (Z) A.624 CH(CH₃)—CH═CH—CH₂Br (E) A.625 CH(CH₃)—CH═CH—CH₂Br (Z) A.626 CH(CH₃)—CCl═CCl—CH₂Cl (E) A.627 CH(CH₃)—CCl═CCl—CH₂Cl (Z) A.628 CH(CH₃)—CF═CH₂ A.629 CH(CH₃)—CH═CH—F (E) A.630 CH(CH₃)—CH═CH—F (Z) A.631 CH(CH₃)—CH═CF₂ A.632 CH(CH₃)—CF═CH—F (E) A.633 CH(CH₃)—CF═CH—F (Z) A.634 CH₂CHCl—CH═CH₂ A.635 CH₂CH₂—CH═C(CH₃)₂ A.636 CH₂CH₂—C(CH₃)═CH—CH₃ (E) A.637 CH₂CH₂—C(CH₃)═CH—CH₃ (Z) A.638 C(CH₃)═CH—[C₆H₅] (E) A.639 C(CH₃)═CH—[2-CN—C₆H₄] (E) A.640 C(CH₃)═CH—[3-CN—C₆H₄] (E) A.641 C(CH₃)═CH—[4-CN—C₆H₄] (E) A.642 C(CH₃)═CH—[2-F—C₆H₄] (E) A.643 C(CH₃)═CH—[3-F—C₆H₄] (E) A.644 C(CH₃)═CH—[4-F—C₆H₄] (E) A.645 C(CH₃)═CH—[2,4-F₂—C₆H₃] (E) A.646 C(CH₃)═CH—[3,4-F₂—C₆H₃] (E) A.647 C(CH₃)═CH—[2,4,5-F₃—C₆H₂] (E) A.648 C(CH₃)═CH—[2,4,6-F₃—C₆H₂] (E) A.649 C(CH₃)═CH—[2-Cl—C₆H₄] (E) A.650 C(CH₃)═CH—[3-Cl—C₆H₄] (E) A.651 C(CH₃)═CH—[4-Cl—C₆H₄] (E) A.652 C(CH₃)═CH—[2,4-Cl₂—C₆H₃] (E) A.653 C(CH₃)═CH—[3,4-Cl₂—C₆H₃] (E) A.654 C(CH₃)═CH—[2,4,5-Cl₃—C₆H₂] (E) A.655 C(CH₃)═CH—[2,4,6-Cl₃—C₆H₂] (E) A.656 C(CH₃)═CH—[2-CH₃—C₆H₄] (E) A.657 C(CH₃)═CH—[3-CH₃—C₆H₄] (E) A.656 C(CH₃)═CH—[4-CH₃—C₆H₄] (E) A.659 C(CH₃)═CH—[2-F, 4-CH₃—C₆H₃] (E) A.660 C(CH₃)═CH—[2-CH₃, 4-F—C₆H₃] (E) A.661 C(CH₃)═CH—[3-F, 4-CH₃—C₆H₃] (E) A.662 C(CH₃)═CH—[3-CH₃, 4-F—C₆H₃] (E) A.663 C(CH₃)═CH—[2-Cl, 4-CH₃—C₆H₃] (E) A.664 C(CH₃)═CH—[2-CH₃, 4-Cl—C₆H₃] (E) A.665 C(CH₃)═CH—[3-Cl, 4-CH₃—C₆H₃] (E) A.666 C(CH₃)═CH—[3-CH₃, 4-Cl—C₆H₃] (E) A.667 C(CH₃)═CH—[2,4-(CH₃)₂—C₆H₃] (E) A.668 C(CH₃)═CH—[3,4-(CH₃)₂—C₆H₃] (E) A.669 C(CH₃)═CH—[2,4,5-(CH₃)₃—C₆H₂] (E) A.670 C(CH₃)═CH—[2,4,6-(CH₃)₃—C₆H₂] (E) A.671 C(CH₃)═CH—[2-CF₃—C₆H₄] (E) A.672 C(CH₃)═CH—[3-CF₃—C₆H₄] (E) A.673 C(CH₃)═CH—[4-CF₃—C₆H₄] (E) A.674 C(CH₃)═CH—[2-F, 4-CF₃—C₆H₃] (E) A.675 C(CH₃)═CH—[2-CF₃, 4-F—C₆H₃] (E) A.676 C(CH₃)═CH—[3-F, 4-CF₃—C₆H₃] (E) A.677 C(CH₃)═CH—[3-CF₃, 4-F—C₆H₃] (E) A.678 C(CH₃)═CH—[2-Cl, 4-CF₃—C₆H₃] (E) A.679 C(CH₃)═CH—[2-CF₃, 4-Cl—C₆H₃] (E) A.680 C(CH₃)═CH—[3-Cl, 4-CF₃—C₆H₃] (E) A.681 C(CH₃)═CH—[3-CF₃, 4-Cl—C₆H₃] (E) A.682 C(CH₃)═CH—[2,4-(CF₃)₂—C₆H₃] (E) A.683 C(CH₃)═CH—[3,4-(CF₃)₂—C₆H₃] (E) A.684 C(CH₃)═CH—[2,4,5-(CF₃)₃—C₆H₂] (E) A.685 C(CH₃)═CH—[2,4,6-(CF₃)₃—C₆H₂] (E) A.686 C(CH₃)═CH—[2-OCH₃—C₆H₄] (E) A.687 C(CH₃)═CH—[3-OCH₃—C₆H₄] (E) A.688 C(CH₃)═CH—[4-OCH₃—C₆H₄] (E) A.689 C(CH₃)═CH—[2-F, 4-OCH₃—C₆H₃] (E) A.690 C(CH₃)═CH—[2-OCH₃, 4-F—C₆H₃] (E) A.691 C(CH₃)═CH—[3-F, 4-OCH₃—C₆H₃] (E) A.692 C(CH₃)═CH—[3-OCH₃, 4-F—C₆H₃] (E) A.693 C(CH₃)═CH—[2-Cl, 4-OCH₃—C₆H₃] (E) A.694 C(CH₃)═CH—[2-OCH₃, 4-Cl—C₆H₃] (E) A.695 C(CH₃)═CH—[3-Cl, 4-OCH₃—C₆H₃] (E) A.696 C(CH₃)═CH—[3-OCH₃, 4-Cl—C₆H₃] (E) A.697 C(CH₃)═CH—[2,4-(OCH₃)₂—C₆H₃] (E) A.698 C(CH₃)═CH—[3,4-(OCH₃)₂—C₆H₃] (E) A.699 C(CH₃)═CH—(2,4,5-(OCH₃)₃—C₆H₂) (E) A.700 C(CH₃)═CH—[2,4,6-(OCH₃)₃—C₆H₂] (E) A.701 C(CH₃)═CH—[2-OCHF₂—C₆H₄] (E) A.702 C(CH₃)═CH—[3-OCHF₂—C₆H₄] (E) A.703 C(CH₃)═CH—[4-OCHF₂—C₆H₄] (E) A.704 C(CH₃)═CH—[2-F, 4-OCHF₂—C₆H₃] (E) A.705 C(CH₃)═CH—[2-OCHF₂, 4-F—C₆H₃] (E) A.706 C(CH₃)═CH—[3-F, 4-OCHF₂—C₆H₃] (E) A.707 C(CH₃)═CH—[3-OCHF₂, 4-F—C₆H₃] (E) A.708 C(CH₃)═CH—[2-Cl, 4-OCHF₂—C₆H₃] (E) A.709 C(CH₃)═CH—[2-OCHF₂, 4-Cl—C₆H₃] (E) A.710 C(CH₃)═CH—[3-Cl, 4-OCHF₂—C₆H₃] (E) A.711 C(CH₃)═CH—[3-OCHF₂, 4-Cl—C₆H₃] (E) A.712 C(CH₃)═CH—[2,4-(OCHF₂)₂—C₆H₃] (E) A.713 C(CH₃)═CH—[3,4-(OCHF₂)₂—C₆H₃] (E) A.714 C(CH₃)═CH—[2,4,5-(OCHF₂)₃—C₆H₂] (E) A.715 C(CH₃)═CH—[2,4,6-(OCHF₂)₃—C₆H₂] (E) A.716 CH═C(CH₃)—[C₆H₅] (E) A.717 CH═C(CH₃)—[2-CN—C₆H₄] (E) A.718 CH═C(CH₃)—[3-CN—C₆H₄] (E) A.719 CH═C(CH₃)—[4-CN—C₆H₄] (E) A.720 CH═C(CH₃)—[2-F—C₆H₄] (E) A.721 CH═C(CH₃)—[3-F—C₆H₄] (E) A.722 CH═C(CH₃)—[4-F—C₆H₄] (E) A.723 CH═C(CH₃)—[2,4-F₂—C₆H₃] (E) A.724 CH═C(CH₃)—[3,4-F₂—C₆H₃] (E) A.725 CH═C(CH₃)—[2,4,5-F₃—C₆H₂] (E) A.726 CH═C(CH₃)—[2,4,6-F₃—C₆H₂] (E) A.727 CH═C(CH₃)—[2-Cl—C₆H₄] (E) A.728 CH═C(CH₃)—[3-Cl—C₆H₄] (E) A.729 CH═C(CH₃)—[4-Cl—C₆H₄] (E) A.730 CH═C(CH₃)—[2,4-Cl₂—C₆H₃] (E) A.731 CH═C(CH₃)—[3,4-Cl₂—C₆H₃] (E) A.732 CH═C(CH₃)—[2,4,5-Cl₃—C₆H₂] (E) A.733 CH═C(CH₃)—[2,4,6-Cl₃—C₆H₂] (E) A.734 CH═C(CH₃)—[2-CH₃—C₆H₄] (E) A.735 CH═C(CH₃)—[3-CH₃—C₆H₄] (E) A.736 CH═C(CH₃)—[4-CH₃—C₆H₄] (E) A.737 CH═C(CH₃)—[2-F, 4-CH₃—C₆H₃] (E) A.738 CH═C(CH₃)—[2-CH₃, 4-F—C₆H₃] (E) A.739 CH═C(CH₃)—[3-F, 4-CH₃—C₆H₃] (E) A.740 CH═C(CH₃)—[3-CH₃, 4-F—C₆H₃] (E) A.741 CH═C(CH₃)—[2-Cl, 4-CH₃—C₆H₃] (E) A.742 CH═C(CH₃)—[2-CH₃, 4-Cl—C₆H₃] (E) A.743 CH═C(CH₃)—[3-Cl, 4-CH₃—C₆H₃] (E) A.744 CH═C(CH₃)—[3-CH₃, 4-Cl—C₆H₃] (E) A.745 CH═C(CH₃)—[2,4-(CH₃)₂—C₆H₃] (E) A.746 CH═C(CH₃)—[3,4-(CH₃)₂—C₆H₃] (E) A.747 CH═C(CH₃)—[2,4,5-(CH₃)₃—C₆H₂] (E) A.748 CH═C(CH₃)—[2,4,6-(CH₃)₃—C₆H₂] (E) A.749 CH═C(CH₃)—[2-CF₃—C₆H₄] (E) A.750 CH═C(CH₃)—[3-CF₃—C₆H₄] (E) A.751 CH═C(CH₃)—[4-CF₃—C₆H₄] (E) A.752 CH═C(CH₃)—[2-F, 4-CF₃—C₆H₃] (E) A.753 CH═C(CH₃)—[2-CF₃, 4-F—C₆H₃] (E) A.754 CH═C(CH₃)—[3-F, 4-CF₃—C₆H₃] (E) A.755 CH═C(CH₃)—[3-CF₃, 4-F—C₆H₃] (E) A.756 CH═C(CH₃)—[2-Cl, 4-CF₃—C₆H₃] (E) A.757 CH═C(CH₃)—[2-CF₃, 4-Cl—C₆H₃] (E) A.758 CH═C(CH₃)—[3-Cl, 4-CF₃—C₆H₃] (E) A.759 CH═C(CH₃)—[3-CF₃, 4-Cl—C₆H₃] (E) A.760 CH═C(CH₃)—[2,4-(CF₃)₂—C₆H₃] (E) A.761 CH═C(CH₃)—[3,4-(CF₃)₂—C₆H₃] (E) A.762 CH═C(CH₃)—[2,4,5-(CF₃)₃—C₆H₂] (E) A.763 CH═C(CH₃)—[2,4,6-(CF₃)₃—C₆H₂] (E) A.764 CH═C(CH₃)—[2-OCH₃—C₆H₄] (E) A.765 CH═C(CH₃)—[3-OCH₃—C₆H₄] (E) A.766 CH═C(CH₃)—[4-OCH₃—C₆H₄] (E) A.767 CH═C(CH₃)—[2-F, 4-OCH₃—C₆H₃] (E) A.768 CH═C(CH₃)—[2-OCH₃, 4-F—C₆H₃] (E) A.769 CH═C(CH₃)—[3-F, 4-OCH₃—C₆H₃] (E) A.770 CH═C(CH₃)—[3-OCH₃, 4-F—C₆H₃] (E) A.771 CH═C(CH₃)—[2-Cl, 4-OCH₃—C₆H₃] (E) A.772 CH═C(CH₃)—[2-OCH₃, 4-Cl—C₆H₃] (E) A.773 CH═C(CH₃)—[3-Cl, 4-OCH₃—C₆H₃] (E) A.774 CH═C(CH₃)—[3-OCH₃, 4-Cl—C₆H₃] (E) A.775 CH═C(CH₃)—[2,4-(OCH₃)₂—C₆H₃] (E) A.776 CH═C(CH₃)—[3,4-(OCH₃)₂—C₆H₃] (E) A.777 CH═C(CH₃)—[2,4,5-(OCH₃)₃—C₆H₂] (E) A.778 CH═C(CH₃)—[2,4,6-(OCH₃)₃—C₆H₂] (E) A.779 CH═C(CH₃)—[2-OCHF₂—C₆H₄] (E) A.780 CH═C(CH₃)—[3-OCHF₂—C₆H₄] (E) A.781 CH═C(CH₃)—[4-OCHF₂—C₆H₄] (E) A.782 CH═C(CH₃)—[2-F, 4-OCHF₂—C₆H₃] (E) A.783 CH═C(CH₃)—[2-OCHF₂, 4-F—C₆H₃] (E) A.784 CH═C(CH₃)—[3-F, 4-OCHF₂—C₆H₃] (E) A.785 CH═C(CH₃)—[3-OCHF₂, 4-F—C₆H₃] (E) A.786 CH═C(CH₃)—[2-Cl, 4-OCHF₂—C₆H₃] (E) A.787 CH═C(CH₃)—[2-OCHF₂, 4-Cl—C₆H₃] (E) A.788 CH═C(CH₃)—[3-Cl, 4-OCHF₂—C₆H₃] (E) A.789 CH═C(CH₃)—[3-OCHF₂, 4-Cl—C₆H₃] (E) A.790 CH═C(CH₃)—[2,4-(OCHF₂)₂—C₆H₃] (E) A.791 CH═C(CH₃)—[3,4-(OCHF₂)₂—C₆H₃] (E) A.792 CH═C(CH₃)—[2,4,5-(OCHF₂)₃—C₆H₂] (E) A.793 CH═C(CH₃)—[2,4,6-(OCHF₂)₃—C₆H₂] (E) A.794 C≡C—I A.795 CH₂—C≡C—H A.796 CH₂—C≡C—Cl A.797 CH₂—C≡C—Br A.798 CH₂—C≡C—I A.799 CH₂—C≡C—CH₃ A.800 CH₂—C≡C—CH₂CH₃ A.801 CH₂CH₂—C≡C—H A.802 CH₂CH₂—C≡C—Cl A.803 CH₂CH₂—C≡C—Br A.804 CH₂CH₂—C≡C—I A.805 CH₂CH₂—C≡C—CH₃ A.806 CH₂CH₂CH₂—C≡C—H A.807 CH₂CH₂CH₂—C≡C—Cl A.808 CH₂CH₂CH₂—C≡C—Br A.809 CH₂CH₂CH₂—C≡C—I A.810 CH₂CH₂CH₂—C≡C—CH₃ A.811 CH(CH₃)—C≡C—H A.812 CH(CH₃)—C≡C—Cl A.813 CH(CH₃)—C≡C—Br A.814 CH(CH₃)—C≡C—I A.815 CH(CH₃)—C≡C—CH₃ A.816 C≡C—[4-F—C₆H₄]

TABLE B No. R² B.1 CH₂CH₃ B.2 CH₂CH₂—CN B.3 CH₂CH₂—O—CH₃ B.4 CH₂CH₂—O—CH₂CH₃ B.5 CH₂CH₂CH₃ B.6 CH(CH₃)₂ B.7 CH₂CH₂CH₂CH₃ B.8 CH(CH₃)CH₂CH₃ B.9 CH₂CH(CH₃)₂ B.10 CH═CH₂ B.11 CH═CH—CH₃ (E) B.12 CH═CH—[C₆H₅] (E) B.13 CH═CH—[2-CN—C₆H₄] (E) B.14 CH═CH—[3-CN—C₆H₄] (E) B.15 CH═CH—[4-CN—C₆H₄] (E) B.16 CH═CH—[2-F—C₆H₄] (E) B.17 CH═CH—[3-F—C₆H₄] (E) B.18 CH═CH—[4-F—C₆H₄] (E) B.19 CH═CH—[2,4-F₂—C₆H₃] (E) B.20 CH═CH—[3,4-F₂—C₆H₃] (E) B.21 CH═CH—[2,4,5-F₃—C₆H₂] (E) B.22 CH═CH—[2,4,6-F₃—C₆H₂] (E) B.23 CH═CH—[2-Cl—C₆H₄] (E) B.24 CH═CH—[3-Cl—C₆H₄] (E) B.25 CH═CH—[4-Cl—C₆H₄] (E) B.26 CH═CH—[2,4-Cl₂—C₆H₃] (E) B.27 CH═CH—[3,4-Cl₂—C₆H₃] (E) B.28 CH═CH—[2,4,5-Cl₃—C₆H₂] (E) B.29 CH═CH—[2,4,6-Cl₃—C₆H₂] (E) B.30 CH═CH—[2-CH₃—C₆H₄] (E) B.31 CH═CH—[3-CH₃—C₆H₄] (E) B.32 CH═CH—[4-CH₃—C₆H₄] (E) B.33 CH═CH—[2-F, 4-CH₃—C₆H₃] (E) B.34 CH═CH—[2-CH₃, 4-F—C₆H₃] (E) B.35 CH═CH—[3-F, 4-CH₃—C₆H₃] (E) B.36 CH═CH—[3-CH₃, 4-F—C₆H₃] (E) B.37 CH═CH—[2-Cl, 4-CH₃—C₆H₃] (E) B.38 CH═CH—[2-CH₃, 4-Cl—C₆H₃] (E) B.39 CH═CH—[3-Cl, 4-CH₃—C₆H₃] (E) B.40 CH═CH—[3-CH₃, 4-Cl—C₆H₃] (E) B.41 CH═CH—[2-CF₃—C₆H₄] (E) B.42 CH═CH—[3-CF₃—C₆H₄] (E) B.43 CH═CH—[4-CF₃—C₆H₄] (E) B.44 CH═CH—[2-OCH₃—C₆H₄] (E) B.45 CH═CH—[3-OCH₃—C₆H₄] (E) B.46 CH═CH—[4-OCH₃—C₆H₄] (E) B.47 CH═CH—[2-OCHF₂—C₆H₄] (E) B.48 CH═CH—[3-OCHF₂—C₆H₄] (E) B.49 CH═CH—[4-OCHF₂—C₆H₄] (E) B.50 CH₂CH═CH₂ B.51 CH₂CH═CH—Cl (E) B.52 CH₂CH═CH—CH₃ (E) B.53 C≡CH B.54 C≡C—Cl B.55 C≡C—Br B.56 C≡C—CH₃ B.57 C≡C—C₆H₅ B.58 C≡C—[2-Cl—C₆H₄] B.59 C≡C—[4-Cl—C₆H₄] B.60 C≡C—[2,4-Cl₂—C₆H₃] B.61 C≡C—[2-CH₃—C₆H₄] B.62 C≡C—[4-CH₃—C₆H₄] B.63 C≡C—[2,4-(CH₃)₂—C₆H₃] B.64 C≡C—[2-Cl, 4-CH₃—C₆H₃] B.65 C≡C—[2-CH₃, 4-Cl—C₆H₃] B.66 C≡C—[3-CF₃—C₆H₄] B.67 C≡C—[3-Cl, 5-CF₃—C₆H₃] B.68 C≡C—[2-OCH₃—C₆H₄] B.69 C≡C—[4-OCH₃—C₆H₄] B.70 C≡C—[2,4-(OCH₃)₂—C₆H₃] B.71 C≡C—[2-Cl, 4-OCH₃—C₆H₃] B.72 C≡C—[2-OCH₃, 4-Cl—C₆H₃] B.73 C═C—[3-OCHF₂—C₆H₄] B.74 C≡C—[3-Cl, 5-OCHF₂—C₆H₃] B.75 cyclopentyl B.76 1-CH₃-cyclopentyl B.77 2-CH₃-cyclopentyl B.78 3-CH₃-cyclopentyl B.79 2,3-(CH₃)₂-cyclopentyl B.80 1-Cl-cyclopentyl B.81 2-Cl-cyclopentyl B.82 3-Cl-cyclopentyl B.83 2-CH₃, 3-Cl-cyclopentyl B.84 2,3-Cl₂-cyclopentyl B.85 cyclohexyl B.86 1-CH₃-cyclohexyl B.87 2-CH₃-cyclohexyl B.88 3-CH₃-cyclohexyl B.89 2,3-(CH₃)₂-cyclohexyl B.90 3,3-(CH₃)₂-cyclohexyl B.91 1-Cl-cyclohexyl B.92 2-Cl-cyclohexyl B.93 3-Cl-cyclohexyl B.94 2-CH₃, 3-Cl-cyclohexyl B.95 2,3-Cl₂-cyclohexyl B.96 C₆H₅ B.97 2-CN—C₆H₄ B.98 3-CN—C₆H₄ B.99 4-CN—C₆H₄ B.100 2-F—C₆H₄ B.101 3-F—C₆H₄ B.102 4-F—C₆H₄ B.103 2,4-F₂—C₆H₃ B.104 3,4-F₂—C₆H₃ B.105 2,4,5-F₃—C₆H₂ B.106 2,4,6-F₃—C₆H₂ B.107 2-Cl—C₆H₄ B.108 3-Cl—C₆H₄ B.109 4-Cl—C₆H₄ B.110 2,4-Cl₂—C₆H₃ B.111 3,4-Cl₂—C₆H₃ B.112 2,4,5-Cl₃—C₆H₂ B.113 2,4,6-Cl₃—C₆H₂ B.114 2-CH₃—C₆H₄ B.115 3-CH₃—C₆H₄ B.116 4-CH₃—C₆H₄ B.117 2-F, 4-CH₃—C₆H₃ B.118 2-CH₃, 4-F—C₆H₃ B.119 3-F, 4-CH₃—C₆H₃ B.120 3-CH₃, 4-F—C₆H₃ B.121 2-Cl, 4-CH₃—C₆H₃ B.122 2-CH₃, 4-Cl—C₆H₃ B.123 3-Cl, 4-CH₃—C₆H₃ B.124 3-CH₃, 4-Cl—C₆H₃ B.125 2,4-(CH₃)₂—C₆H₃ B.126 3,4-(CH₃)₂—C₆H₃ B.127 2,4,5-(CH₃)₃—C₆H₂ B.128 2,4,6-(CH₃)₃—C₆H₂ B.129 2-CF₃—C₆H₄ B.130 3-CF₃—C₆H₄ B.131 4-CF₃—C₆H₄ B.132 2-F, 4-CF₃—C₆H₃ B.133 2-CF₃, 4-F—C₆H₃ B.134 3-F, 4-CF₃—C₆H₃ B.135 3-CF₃, 4-F—C₆H₃ B.136 2-Cl, 4-CF₃—C₆H₃ B.137 2-CF₃, 4-Cl—C₆H₃ B.138 3-Cl, 4-CF₃—C₆H₃ B.139 3-CF₃, 4-Cl—C₆H₃ B.140 2,4-(CF₃)₂—C₆H₃ B.141 3,4-(CF₃)₂—C₆H₃ B.142 2,4,5-(CF₃)₃—C₆H₂ B.143 2,4,6-(CF₃)₃—C₆H₂ B.144 2-OCH₃—C₆H₄ B.145 3-OCH₃—C₆H₄ B.146 4-OCH₃—C₆H₄ B.147 2-F, 4-OCH₃—C₆H₃ B.148 2-OCH₃, 4-F—C₆H₃ B.149 3-F, 4-OCH₃—C₆H₃ B.150 3-OCH₃, 4-F—C₆H₃ B.151 2-Cl, 4-OCH₃—C₆H₃ B.152 2-OCH₃, 4-Cl—C₆H₃ B.153 3-Cl, 4-OCH₃—C₆H₃ B.154 3-OCH₃, 4-Cl—C₆H₃ B.155 2,4-(OCH₃)₂—C₆H₃ B.156 3,4-(OCH₃)₂—C₆H₃ B.157 2,4,5-(OCH₃)₃—C₆H₂ B.158 2,4,6-(OCH₃)₃—C₆H₂ B.159 2-OCHF₂—C₆H₄ B.160 3-OCHF₂—C₆H₄ B.161 4-OCHF₂—C₆H₄ B.162 2-F, 4-OCHF₂—C₆H₃ B.163 2-OCHF₂, 4-F—C₆H₃ B.164 3-F, 4-OCHF₂—C₆H₃ B.165 3-OCHF₂, 4-F—C₆H₃ B.166 2-Cl, 4-OCHF₂—C₆H₃ B.167 2-OCHF₂, 4-Cl—C₆H₃ B.168 3-Cl, 4-OCHF₂—C₆H₃ B.169 3-OCHF₂, 4-Cl—C₆H₃ B.170 2,4-(OCHF₂)₂—C₆H₃ B.171 3,4-(OCHF₂)₂—C₆H₃ B.172 2,4,5-(OCHF₂)₃—C₆H₂ B.173 2,4,6-(OCHF₂)₃—C₆H₂ B.174 CH₂—C₆H₅ B.175 CH₂—[2-CN—C₆H₄] B.176 CH₂—[3-CN—C₆H₄] B.177 CH₂—[4-CN—C₆H₄] B.178 CH₂—[2-F—C₆H₄] B.179 CH₂—[3-F—C₆H₄] B.180 CH₂—[4-F—C₆H₄] B.181 CH₂—[2,4-F₂—C₆H₃] B.182 CH₂—[3,4-F₂—C₆H₃] B.183 CH₂—[2,4,5-F₃—C₆H₂] B.184 CH₂—[2,4,6-F₃—C₆H₂] B.185 CH₂—[2-Cl—C₆H₄] B.186 CH₂—[3-Cl—C₆H₄] B.187 CH₂—[4-Cl—C₆H₄] B.188 CH₂—[2,4-Cl₂—C₆H₃] B.189 CH₂—[3,4-Cl₂—C₆H₃] B.190 CH₂—[2,4,5-Cl₃—C₆H₂] B.191 CH₂—[2,4,6-Cl₃—C₆H₂] B.192 CH₂—[2-CH₃—C₆H₄] B.193 CH₂—[3-CH₃—C₆H₄] B.194 CH₂—[4-CH₃—C₆H₄] B.195 CH₂—[2-F, 4-CH₃—C₆H₃] B.196 CH₂—[2-CH₃, 4-F—C₆H₃] B.197 CH₂—[3-F, 4-CH₃—C₆H₃] B.198 CH₂—[3-CH₃, 4-F—C₆H₃] B.199 CH₂—[2-Cl, 4-CH₃—C₆H₃] B.200 CH₂—[2-CH₃, 4-Cl—C₆H₃] B.201 CH₂—[3-Cl, 4-CH₃—C₆H₃] B.202 CH₂—[3-CH₃, 4-Cl—C₆H₃] B.203 CH₂—[2-CF₃—C₆H₄] B.204 CH₂—[3-CF₃—C₆H₄] B.205 CH₂—[4-CF₃—C₆H₄] B.206 CH₂—[2-OCH₃—C₆H₄] B.207 CH₂—[3-OCH₃—C₆H₄] B.208 CH₂—[4-OCH₃—C₆H₄] B.209 CH₂—[2-OCHF₂—C₆H₄] B.210 CH₂—[3-OCHF₂—C₆H₄] B.211 CH₂—[4-OCHF₂—C₆H₄] B.212 CH(CH₃)—C₆H₅ B.213 CH(CH₃)—[2-CN—C₆H₄] B.214 CH(CH₃)—[3-CN—C₆H₄] B.215 CH(CH₃)—[4-CN—C₆H₄] B.216 CH(CH₃)—[2-F—C₆H₄] B.217 CH(CH₃)—[3-F—C₆H₄] B.218 CH(CH₃)—[4-F—C₆H₄] B.219 CH(CH₃)—[2,4-F₂—C₆H₃] B.220 CH(CH₃)—[3,4-F₂—C₆H₃] B.221 CH(CH₃)—[2,4,5-F₃—C₆H₂] B.222 CH(CH₃)—[2,4,6-F₃—C₆H₂] B.223 CH(CH₃)—[2-Cl—C₆H₄] B.224 CH(CH₃)—[3-Cl—C₆H₄] B.225 CH(CH₃)—[4-Cl—C₆H₄] B.226 CH(CH₃)—[2,4-Cl₂—C₆H₃] B.227 CH(CH₃)—[3,4-Cl₂—C₆H₃] B.228 CH(CH₃)—[2,4,5-Cl₃—C₆H₂] B.229 CH(CH₃)—[2,4,6-Cl₃—C₆H₂] B.230 CH(CH₃)—[2-CH₃—C₆H₄] B.231 CH(CH₃)—[3-CH₃—C₆H₄] B.232 CH(CH₃)—[4-CH₃—C₆H₄] B.233 CH(CH₃)—[2-F, 4-CH₃—C₆H₃] B.234 CH(CH₃)—[2-CH₃, 4-F—C₆H₃] B.235 CH(CH₃)—[3-F, 4-CH₃—C₆H₃] B.236 CH(CH₃)—[3-CH₃, 4-F—C₆H₃] B.237 CH(CH₃)—[2-Cl, 4-CH₃—C₆H₃] B.238 CH(CH₃)—[2-CH₃, 4-Cl—C₆H₃] B.239 CH(CH₃)—[3-Cl, 4-CH₃—C₆H₃] B.240 CH(CH₃)—[3-CH₃, 4-Cl—C₆H₃] B.241 CH(CH₃)—[2-CF₃—C₆H₄] B.242 CH(CH₃)—[3-CF₃—C₆H₄] B.243 CH(CH₃)—[4-CF₃—C₆H₄] B.244 CH(CH₃)—[2-OCH₃—C₆H₄] B.245 CH(CH₃)—[3-OCH₃—C₆H₄] B.246 CH(CH₃)—[4-OCH₃—C₆H₄] B.247 CH(CH₃)—[2-OCHF₂—C₆H₄] B.248 CH(CH₃)—[3-OCHF₂—C₆H₄] B.249 CH(CH₃)—[4-OCHF₂—C₆H₄] B.250 CH₂F B.251 CHF₂ B.252 CF₃ B.253 CH₂—CN B.254 CH₂—OCH₃ B.255 CH₂—OCH₂CH₃ B.256 CH₂—OCH₂CH₂CH₃ B.257 CH₂—OCH(CH₃)₂ B.258 CH₂—OCH₂CH₂CH₂CH₃ B.259 CH₂—OCH(CH₃)CH₂CH₃ B.260 CH₂—OCH₂CH(CH₃)₂ B.261 CH₂—OC(CH₃)₃ B.262 CH₂—OCF₃ B.263 CH₂—OCH₂CF₃ B.264 CH₂CH₂—OCH₂CH₂CH₃ B.265 CH₂CH₂—OCH(CH₃)₂ B.266 CH₂CH₂—OCH₂CH₂CH₂CH₃ B.267 CH₂CH₂—OCH(CH₃)CH₂CH₃ B.268 CH₂CH₂—OCH₂CH(CH₃)₂ B.269 CH₂CH₂—OC(CH₃)₃ B.270 CH₂CH₂—OCF₃ B.271 CH₂CH₂—OCH₂CF₃ B.272 CH₂CH₂—[C₆H₅] B.273 CH₂CH₂—[2-CN—C₆H₄] B.274 CH₂CH₂—[3-CN—C₆H₄] B.275 CH₂CH₂—[4-CN—C₆H₄] B.276 CH₂CH₂—[2-F—C₆H₄] B.277 CH₂CH₂—[3-F—C₆H₄] B.278 CH₂CH₂—[4-F—C₆H₄] B.279 CH₂CH₂—[2,4-F₂—C₆H₃] B.280 CH₂CH₂—[3,4-F₂—C₆H₃] B.281 CH₂CH₂—[2,4,5-F₃—C₆H₂] B.282 CH₂CH₂—[2,4,6-F₃—C₆H₂] B.283 CH₂CH₂—[2-Cl—C₆H₄] B.284 CH₂CH₂—[3-Cl—C₆H₄] B.285 CH₂CH₂—[4-Cl—C₆H₄] B.286 CH₂CH₂—[2,4-Cl₂—C₆H₃] B.287 CH₂CH₂—[3,4-Cl₂—C₆H₃] B.288 CH₂CH₂—[2,4,5-Cl₃—C₆H₂] B.289 CH₂CH₂—[2,4,6-Cl₃—C₆H₂] B.290 CH₂CH₂—[2-CH₃—C₆H₄] B.291 CH₂CH₂—[3-CH₃—C₆H₄] B.292 CH₂CH₂—[4-CH₃—C₆H₄] B.293 CH₂CH₂—[2-F, 4-CH₃—C₆H₃] B.294 CH₂CH₂—[2-CH₃, 4-F—C₆H₃] B.295 CH₂CH₂—[3-F, 4-CH₃—C₆H₃] B.296 CH₂CH₂—[3-CH₃, 4-F—C₆H₃] B.297 CH₂CH₂—[2-Cl, 4-CH₃—C₆H₃] B.298 CH₂CH₂—[2-CH₃, 4-Cl—C₆H₃] B.299 CH₂CH₂—[3-Cl, 4-CH₃—C₆H₃] B.300 CH₂CH₂—[3-CH₃, 4-Cl—C₆H₃] B.301 CH₂CH₂—[2-CF₃—C₆H₄] B.302 CH₂CH₂—[3-CF₃—C₆H₄] B.303 CH₂CH₂—[4-CF₃—C₆H₄] B.304 CH₂CH₂—[2-OCH₃—C₆H₄] B.305 CH₂CH₂—[3-OCH₃—C₆H₄] B.306 CH₂CH₂—[4-OCH₃—C₆H₄] B.307 CH₂CH₂—[2-OCHF₂—C₆H₄] B.308 CH₂CH₂—[3-OCHF₂—C₆H₄] B.309 CH₂CH₂—[4-OCHF₂—C₆H₄] B.310 CH(CH₃)—CN B.311 CH(CH₃)—OCH₃ B.312 CH(CH₃)—OCH₂CH₃ B.313 CH(CH₃)—OCH₂CH₂CH₃ B.314 CH(CH₃)—OCH(CH₃)₂ B.315 CH(CH₃)—OCH₂CH₂CH₂CH₃ B.316 CH(CH₃)—OCH(CH₃)CH₂CH₃ B.317 CH(CH₃)—OCH₂CH(CH₃)₂ B.318 CH(CH₃)—OC(CH₃)₃ B.319 CH(CH₃)—OCF₃ B.320 CH(CH₃)—OCH₂CF₃ B.321 CH₂CH₂F B.322 CH₂CHF₂ B.323 CH₂CF₃ B.324 CHFCH₃ B.325 CF₂CH₃ B.326 CHFCHF₂ B.327 CHFCF₃ B.328 CF₂CHF₂ B.329 CF₂CF₃ B.330 CF₂CHFCl B.331 CH₂CH₂CH₂—CN B.332 CH₂CH₂CH₂—OCH₃ B.333 CH₂CH₂CH₂—OCH₂CH₃ B.334 CH₂CH₂CH₂—OCH₂CH₂CH₃ B.335 CH₂CH₂CH₂—OCH(CH₃)₂ B.336 CH₂CH₂CH₂—OCF₃ B.337 CH₂CH₂CH₂—OCH₂CF₃ B.338 CH₂CH(CH₃)—CN B.339 CH₂CH(CH₃)—OCH₃ B.340 CH₂CH(CH₃)—OCH₂CH₃ B.341 CH₂CH(CH₃)—OCH₂CH₂CH₃ B.342 CH₂CH(CH₃)—OCH(CH₃)₂ B.343 CH₂CH(CH₃)—OCF₃ B.344 CH₂CH(CH₃)—OCH₂CF₃ B.345 CH(CH₂CH₃)—CN B.346 CH(CH₂CH₃)—OCH₃ B.347 CH(CH₂CH₃)—OCH₂CH₃ B.348 CH(CH₂CH₃)—OCH₂CH₂CH₃ B.349 CH(CH₂CH₃)—OCH(CH₃)₂ B.350 CH(CH₂CH₃)—OCF₃ B.351 CH(CH₂CH₃)—OCH₂CF₃ B.352 CH(CH₃)CH₂—CN B.353 CH(CH₃)CH₂—OCH₃ B.354 CH(CH₃)CH₂—OCH₂CH₃ B.355 CH(CH₃)CH₂—OCH₂CH₂CH₃ B.356 CH(CH₃)CH₂—OCH(CH₃)₂ B.357 CH(CH₃)CH₂—OCF₃ B.358 CH(CH₃)CH₂—OCH₂CF₃ B.359 CH₂CH₂CF₃ B.360 CH₂CF₃CF₃ B.361 CHFCH₂CH₃ B.362 CH(CF₃)CH₃ B.363 CH(CF₃)₂ B.364 CH₂CH₂CH₂CH₂—CN B.365 CH₂CH₂CH₂CH₂—OCH₃ B.366 CH₂CH₂CH₂CH₂—OCH₂CH₃ B.367 CH₂CH₂CH₂CH₂—OCF₃ B.368 CH(CN)—CH₂CH₂CH₃ B.369 CH(OCH₃)—CH₂CH₂CH₃ B.370 CH(OCH₂CH₃)—CH₂CH₂CH₃ B.371 CH(OCF₃)—CH₂CH₂CH₃ B.372 CH(OCH₂CF₃)—CH₂CH₂CH₃ B.373 CH(CN)—CH₂CH(CH₃)₂ B.374 CH(OCH₃)—CH₂CH(CH₃)₂ B.375 CH(OCH₂CH₃)—CH₂CH(CH₃)₂ B.376 CH(OCF₃)—CH₂CH(CH₃)₂ B.377 CH(OCH₂CF₃)—CH₂CH(CH₃)₂ B.378 CHFCH₂CH₂CH₃ B.379 C(CH₃)═CH₂ B.380 CH═CH—CH₃ (Z) B.381 C(CH₂CH₃)═CH₂ B.382 C(CH₃)═CH—CH₃ (E) B.383 C(CH₃)═CH—CH₃ (Z) B.384 C(CH₃)═C(CH₃)₂ B.385 CH(CH₃)—CH═CH₂ B.386 CH═C(CH₃)₂ B.387 CH₂—C(CH₃)═CH₂ B.388 CH(CH₃)—CH₂—CH═CH₂ B.389 CH₂—CH(CH₃)—CH═CH₂ B.390 CH₂—CCl═CH₂ B.391 CH₂—CH═CH—Cl (Z) B.392 CH₂—CCl═CH—Cl (E) B.393 CH₂—CCl═CH—Cl (Z) B.394 CH₂—CH═CCl₂ B.395 CH₂—CCl═CCl₂ B.396 CH₂—CBr═CH₂ B.397 CH₂—CH═CH—Br (Z) B.398 CH₂—CBr═CH—Br (E) B.399 CH₂—CBr═CH—Br (Z) B.400 CH₂—CH═CBr₂ B.401 CH₂—CBr═CBr₂ B.402 CH₂—CH═CH—CH₃ (Z) B.403 CH₂—C(CH₃)═CH—CH₃ (E) B.404 CH₂—C(CH₃)═CH—CH₃ (Z) B.405 CH₂—CH═C(CH₃)₂ B.406 CH₂—CH₂—CH═CH₂ B.407 CH₂—CCl═CH—CH₃ (E) B.408 CH₂—CCl═CH—CH₃ (Z) B.409 CH₂—CH═CCl—CH₃ (E) B.410 CH₂—CH═CCl—CH₃ (Z) B.411 CH₂—C(CH₃)═C(CH₃)₂ B.412 CH₂—CBr═CH—CH₃ (E) B.413 CH₂—CBr═CH—CH₃ (Z) B.414 CH₂—CH═CBr—CH₃ (E) B.415 CH₂—CH═CBr—CH₃ (Z) B.416 CH₂—CH═CH—CH₂Cl (E) B.417 CH₂—CH═CH—CH₂Cl (Z) B.418 CH₂—CH═CH—CH₂CH₃ (E) B.419 CH₂—CH═CH—CH₂CH₃ (Z) B.420 CH₂—CH═CH—CH₂Br (E) B.421 CH₂—CH═CH—CH₂Br (Z) B.422 CH₂—CCl═CCl—CH₂Cl (E) B.423 CH₂—CCl═CCl—CH₂Cl (Z) B.424 CH₂—CF═CH₂ B.425 CH₂—CH═CH—F (E) B.426 CH₂—CH═CH—F (Z) B.427 CH₂—CH═CF₂ B.428 CH₂—CF═CH—F (E) B.429 CH₂—CF═CH—F (Z) B.430 CH(CH₃)—CH═CH₂ B.431 CH(CH₃)—CCl═CH₂ B.432 CH(CH₃)—CH═CH—Cl (E) B.433 CH(CH₃)—CH═CH—Cl (Z) B.434 CH(CH₃)—CCl═CH—Cl (E) B.435 CH(CH₃)—CCl═CH—Cl (Z) B.436 CH(CH₃)—CH═CCl₂ B.437 CH(CH₃)—CCl═CCl₂ B.438 CH(CH₃)—CBr═CH₂ B.439 CH(CH₃)—CH═CH—Br (E) B.440 CH(CH₃)—CH═CH—Br (Z) B.441 CH(CH₃)—CBr═CH—Br (E) B.442 CH(CH₃)—CBr═CH—Br (Z) B.443 CH(CH₃)—CH═CBr₂ B.444 CH(CH₃)—CBr═CBr₂ B.445 CH(CH₃)—C(CH₃)═CH₂ B.446 CH(CH₃)—CH═CH—CH₃ (E) B.447 CH(CH₃)—CH═CH—CH₃ (Z) B.448 CH(CH₃)—C(CH₃)═CH—CH₃ (E) B.449 CH(CH₃)—C(CH₃)═CH—CH₃ (Z) B.450 CH(CH₃)—CH═C(CH₃)₂ B.451 CH(CH₃)—CCl═CH—CH₃ (E) B.452 CH(CH₃)—CCl═CH—CH₃ (Z) B.453 CH(CH₃)—CH═CCl—CH₃ (E) B.454 CH(CH₃)—CH═CCl—CH₃ (Z) B.455 CH(CH₃)—CBr═CH—CH₃ (E) B.456 CH(CH₃)—CBr═CH—CH₃ (Z) B.457 CH(CH₃)—CH═CBr—CH₃ (E) B.458 CH(CH₃)—CH═CBr—CH₃ (Z) B.459 CH(CH₃)—CH═CH—CH₂Cl (E) B.460 CH(CH₃)—CH═CH—CH₂Cl (Z) B.461 CH(CH₃)—CH═CH—CH₂CH₃ (E) B.462 CH(CH₃)—CH═CH—CH₂CH₃ (Z) B.463 CH(CH₃)—CH═CH—CH₂Br (E) B.464 CH(CH₃)—CH═CH—CH₂Br (Z) B.465 CH(CH₃)—CCl═CCl—CH₂Cl (E) B.466 CH(CH₃)—CCl═CCl—CH₂Cl (Z) B.467 CH(CH₃)—CF═CH₂ B.468 CH(CH₃)—CH═CH—F (E) B.469 CH(CH₃)—CH═CH—F (Z) B.470 CH(CH₃)—CH═CF₂ B.471 CH(CH₃)—CF═CH—F (E) B.472 CH(CH₃)—CF═CH—F (Z) B.473 CH₂CHCl—CH═CH₂ B.474 CH₂CH₂—CH═C(CH₃)₂ B.475 CH₂CH₂—C(CH₃)═CH—CH₃ (E) B.476 CH₂CH₂—C(CH₃)═CH—CH₃ (Z) B.477 C(CH₃)═CH—[C₆H₅] (E) B.478 C(CH₃)═CH—[2-CN—C₆H₄] (E) B.479 C(CH₃)═CH—[3-CN—C₆H₄] (E) B.480 C(CH₃)═CH—[4-CN—C₆H₄] (E) B.481 C(CH₃)═CH—[2-F—C₆H₄] (E) B.482 C(CH₃)═CH—[3-F—C₆H₄] (E) B.483 C(CH₃)═CH—[4-F—C₆H₄] (E) B.484 C(CH₃)═CH—[2,4-F₂—C₆H₃] (E) B.485 C(CH₃)═CH—[3,4-F₂—C₆H₃] (E) B.486 C(CH₃)═CH—[2,4,5-F₃—C₆H₂] (E) B.487 C(CH₃)═CH—[2,4,6-F₃—C₆H₂] (E) B.488 C(CH₃)═CH—[2-Cl—C₆H₄] (E) B.489 C(CH₃)═CH—[3-Cl—C₆H₄] (E) B.490 C(CH₃)═CH—[4-Cl—C₆H₄] (E) B.491 C(CH₃)═CH—[2,4-Cl₂—C₆H₃] (E) B.492 C(CH₃)═CH—[3,4-Cl₂—C₆H₃] (E) B.493 C(CH₃)═CH—[2,4,5-Cl₃—C₆H₂] (E) B.494 C(CH₃)═CH—[2,4,6-Cl₃—C₆H₂] (E) B.495 C(CH₃)═CH—[2-CH₃—C₆H₄] (E) B.496 C(CH₃)═CH—[3-CH₃—C₆H₄] (E) B.497 C(CH₃)═CH—[4-CH₃—C₆H₄] (E) B.496 C(CH₃)═CH—[2-F, 4-CH₃—C₆H₃] (E) B.499 C(CH₃)═CH—[2-CH₃, 4-F—C₆H₃] (E) B.500 C(CH₃)═CH—[3-F, 4-CH₃—C₆H₃] (E) B.501 C(CH₃)═CH—[3-CH₃, 4-F—C₆H₃] (E) B.502 C(CH₃)═CH—[2-Cl, 4-CH₃—C₆H₃] (E) B.503 C(CH₃)═CH—[2-CH₃, 4-Cl—C₆H₃] (E) B.504 C(CH₃)═CH—[3-Cl, 4-CH₃—C₆H₃] (E) B.505 C(CH₃)═CH—[3-CH₃, 4-Cl—C₆H₃] (E) B.506 C(CH₃)═CH—[2-CF₃—C₆H₄] (E) B.507 C(CH₃)═CH—[3-CF₃—C₆H₄] (E) B.508 C(CH₃)═CH—[4-CF₃—C₆H₄] (E) B.509 C(CH₃)═CH—[2-OCH₃—C₆H₄] (E) B.510 C(CH₃)═CH—[3-OCH₃—C₆H₄] (E) B.511 C(CH₃)═CH—[4-OCH₃—C₆H₄] (E) B.512 C(CH₃)═CH—[2-OCHF₂—C₆H₄] (E) B.513 C(CH₃)═CH—[3-OCHF₂—C₆H₄] (E) B.514 C(CH₃)═CH—[4-OCHF₂—C₆H₄] (E) B.515 CH═C(CH₃)—[C₆H₅] (E) B.516 CH═C(CH₃)—[2-CN—C₆H₄] (E) B.517 CH═C(CH₃)—[3-CN—C₆H₄] (E) B.518 CH═C(CH₃)—[4-CN—C₆H₄] (E) B.519 CH═C(CH₃)—[2-F—C₆H₄] (E) B.520 CH═C(CH₃)—[3-F—C₆H₄] (E) B.521 CH═C(CH₃)—[4-F—C₆H₄] (E) B.522 CH═C(CH₃)—[2,4-F₂—C₆H₃] (E) B.523 CH═C(CH₃)—[3,4-F₂—C₆H₃] (E) B.524 CH═C(CH₃)—[2,4,5-F₃—C₆H₂] (E) B.525 CH═C(CH₃)—[2,4,6-F₃—C₆H₂] (E) B.526 CH═C(CH₃)—[2-Cl—C₆H₄] (E) B.527 CH═C(CH₃)—[3-Cl—C₆H₄] (E) B.528 CH═C(CH₃)—[4-Cl—C₆H₄] (E) B.529 CH═C(CH₃)—[2,4-Cl₂—C₆H₃] (E) B.530 CH═C(CH₃)—[3,4-Cl₂—C₆H₃] (E) B.531 CH═C(CH₃)—[2,4,5-Cl₃—C₆H₂] (E) B.532 CH═C(CH₃)—[2,4,6-Cl₃—C₆H₂] (E) B.533 CH═C(CH₃)—[2-CH₃—C₆H₄] (E) B.534 CH═C(CH₃)—[3-CH₃—C₆H₄] (E) B.535 CH═C(CH₃)—[4-CH₃—C₆H₄] (E) B.536 CH═C(CH₃)—[2-F, 4-CH₃—C₆H₃] (E) B.537 CH═C(CH₃)—[2-CH₃, 4-F—C₆H₃] (E) B.538 CH═C(CH₃)—[3-F, 4-CH₃—C₆H₃] (E) B.539 CH═C(CH₃)—[3-CH₃, 4-F—C₆H₃] (E) B.540 CH═C(CH₃)—[2-Cl, 4-CH₃—C₆H₃] (E) B.541 CH═C(CH₃)—[2-CH₃, 4-Cl—C₆H₃] (E) B.542 CH═C(CH₃)—[3-Cl, 4-CH₃—C₆H₃] (E) B.543 CH═C(CH₃)—[3-CH₃, 4-Cl—C₆H₃] (E) B.544 CH═C(CH₃)—[2-CF₃—C₆H₄] (E) B.545 CH═C(CH₃)—[3-CF₃—C₆H₄] (E) B.546 CH═C(CH₃)—[4-CF₃—C₆H₄] (E) B.547 CH═C(CH₃)—[2-OCH₃—C₆H₄] (E) B.548 CH═C(CH₃)—[3-OCH₃—C₆H₄] (E) B.549 CH═C(CH₃)—[4-OCH₃—C₆H₄] (E) B.550 CH═C(CH₃)—[2-OCHF₂—C₆H₄] (E) B.551 CH═C(CH₃)—[3-OCHF₂—C₆H₄] (E) B.552 CH═C(CH₃)—[4-OCHF₂—C₆H₄] (E) B.553 C≡C—I B.554 CH₂—C≡C—H B.555 CH₂—C≡C—Cl B.556 CH₂—C≡C—Br B.557 CH₂—C≡C—I B.558 CH₂—C≡C—CH₃ B.559 CH₂—C≡C—CH₂CH₃ B.560 CH₂CH₂—C≡C—H B.561 CH₂CH₂—C≡C—Cl B.562 CH₂CH₂—C≡C—Br B.563 CH₂CH₂—C≡C—I B.564 CH₂CH₂—C≡C—CH₃ B.565 CH₂CH₂CH₂—C≡C—H B.566 CH₂CH₂CH₂—C≡C—Cl B.567 CH₂CH₂CH₂—C≡C—Br B.568 CH₂CH₂CH₂—C≡C—I B.569 CH₂CH₂CH₂—C≡C—CH₃ B.570 CH(CH₃)—C≡C—H B.571 CH(CH₃)—C≡C—Cl B.572 CH(CH₃)—C≡C—Br B.573 CH(CH₃)—C≡C—I B.574 CH(CH₃)—C≡C—CH₃ B.575 C≡C—[4-F—C₆H₄]

The compounds I are suitable as fungicides. They are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically, and they can be employed in crop protection as foliar- and soil-acting fungicides.

They are especially important for controlling a large number of fungi on a variety of crop plants such as wheat, rye, barley, oats, rice, maize, grass, bananas, cotton, soya, coffee, sugar cane, grapevines, fruit species, ornamentals and vegetables such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants.

Specifically, they are suitable for controlling the following plant diseases:

Alternaria species on vegetables and fruit,

Botrytis cinerea (gray mold) on strawberries, vegetables, ornamentals and grapevines,

Cercospora arachidicola on peanuts,

Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits,

Erysiphe graminis (powdery mildew) on cereals,

Fusarium and Verticillium species on various plants,

Helminthosporium species on cereals,

Mycosphaerella species on bananas,

Phytophthora infestans on potatoes and tomatoes,

Plasmopara viticola on grapevines,

Podosphaera leucotricha on apples,

Pseudocercosporella herpotrichoides on wheat and barley,

Pseudocercosporella species on hops and cucumbers,

Puccinia species on cereals,

Pyricularia oryzae on rice,

Rhizoctonia species on cotton, rice and lawns,

Septoria nodorum on wheat,

Uncinula necator on grapevines,

Ustilago species on cereals and sugar cane, and

Venturia inaequalis (scab) on apples.

Moreover, the compounds I are suitable for controlling harmful fungi in the protection of materials (eg. wood, paper, paint dispersions, fibers and tissues) and in the protection of stored products.

The compounds I are applied by treating the fungi, or the plants, seeds, materials or the soil to be protected against fungal infection, with a fungicidally active amount of the active ingredients. Application can be effected both before and after infection of the materials, plants or seeds by the fungi.

In general, the fungicidal compositions comprise from 0.1 to 95, preferably 0.5 to 90, % by weight of active ingredient.

When used in crop protection, the rates of application are from 0.01 to 2.0 kg of active ingredient per ha, depending on the nature of the effect desired.

In the treatment of seed, amounts of active ingredient of from 0.001 to 0.1 g, preferably 0.01 to 0.05 g, are generally required per kilogram of seed.

When used in the protection of materials or stored products, the rate of application of active ingredient depends on the nature of the field of application and on the effect desired. Rates of application conventionally used in the protection of materials are, for example, from 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active ingredient per cubic meter of material treated.

Moreover, the compounds of the formula I are suitable for efficiently controlling animal pests from the classes of the insects, arachnids and nematodes. They can be employed in crop protection and in the hygiene, stored-product and veterinary sector for controlling animal pests. In particular, they are suitable for controlling the following animal pests:

insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis,

beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria,

dipterans (Diptera), for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa,

thrips (Thysanoptera), eg. Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,

hymenopterans (Hymenoptera), eg. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,

heteropterans (Heteroptera), eg. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor,

homopterans (Homoptera), eg. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum and Viteus vitifolii,

termites (Isoptera), eg. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus und Termes natalensis,

orthopterans (Orthoptera), eg. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus,

Arachnoidea, such as arachnids (Acarina), eg. Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae,

nematodes such as root knot nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stem eelworms and foliar nematodes, eg. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.

The rate of application of active ingredient for controlling animal pests is from 0.1 to 2.0, preferably 0.2 to 1.0, kg/ha under field conditions.

The compounds I can be converted into the customary formulations, eg. solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular purpose; in any case, it should guarantee a fine and uniform distribution of the compound according to the invention.

The formulations are prepared in a known manner, eg. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as the diluent. Auxiliaries which are suitable are essentially: solvents such as aromatics (eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg. mineral oil fractions), alcohols (eg. methanol, butanol), ketones (eg. cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (eg. kaolins, clays, talc, chalk) and ground synthetic minerals (eg. highly-disperse silica, silicates); emulsifiers such as non-ionic and anionic emulsifiers (eg. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.

Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of napthalenesulfonic acid with phenol or formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.

Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.

Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Examples of solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, eg. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

In general, the formulations comprise of from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The following are exemplary formulations:

I. 5 parts by weight of a compound according to the invention are mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust which comprises 5% by weight of the active ingredient.

II. 30 parts by weight of a compound according to the invention are mixed intimately with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which had been sprayed onto the surface of this silica gel. This gives a formulation of the active ingredient with good adhesion properties (comprises 23% by weight of active ingredient).

III. 10 parts by weight of a compound according to the invention are dissolved in a mixture composed of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 9% by weight of active ingredient).

IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 16% by weight of active ingredient).

V. 80 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill (comprises 80% by weight of active ingredient).

VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone, which gives a solution which is suitable for use in the form of microdrops (comprises 90% by weight of active ingredient).

VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

VIII. 20 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient.

The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, eg. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; in any case, this is intended to guarantee the finest possible distribution of the active ingredients according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.

The active ingredient concentrations in the ready-to-use products can be varied within substantial ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

The active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even the active ingredient without additives.

Various types of oils, herbicides, fungicides, other pesticides, or bactericides may be added to the active ingredients, if appropriate also only immediately prior to use (tank mix). These auxiliaries and agents can be admixed with the active ingredients according to the invention in a weight ratio of 1:10 to 10:1.

In the use form as fungicides, the compositions according to the invention can also be present together with other active ingredients, eg. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. Mixing the compounds I or the compositions comprising them in the use form as fungicides with other fungicides frequently results in a broader fungicidal spectrum of action.

The following list of fungicides together with which the compounds according to the invention can be used is intended to illustrate the possible combinations, but not to impose any limitation:

sulfur, dithiocarbamates and their derivatives, such as iron(III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N′-propylenebisdithiocarbamate), zinc (N,N′-propylenebisdithiocarbamate), N,N′-polypropylenebis(thiocarbamoyl)disulfide;

nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, diisopropyl 5-nitro-isophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2-(2-furyl)-benzimidazole, 2-(4-thiazolyl)-benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-trichloromethylthio-tetrahydrophthalimide, N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfodiamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-thiol 1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl-2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis-1-(2,2,2-trichloroethyl)formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichlorethane; 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N′-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, (2RS,3RS)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)-oxiran-2-ylmethyl]-1H-1,2,4-triazole, α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene,

strobilurins such as methyl E-methoxyimino-[α-(o-tolyloxy)-o-tolyl]acetate, methyl E-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate, N-methyl-E-methoxyimino-[α-(2-phenoxyphenyl)]-acetamide, N-methyl-E-methoxyimino-[α-(2,5-dimethylphenoxy)-o-tolyl]acetamide,

anilinopyrimidines such as N-(4,6-dimethylpyrimidin-2-yl)aniline, N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]-aniline, N-[4-methyl-6-cyclopropylpyrimidin-2-yl]aniline,

phenylpyrroles such as 4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile,

cinnamamides such as 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloylmorpholine,

and a variety of fungicides such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide, hexachlorobenzene, methyl N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate, DL-N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)-alanine methyl ester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichlorophenyl(5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]acetamide, 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole, 2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

MODE(S) FOR CARRYINIG OUT THE INVENTION SYNTHESIS EXAMPLES

With due modification of the starting compounds, the protocols shown in the synthesis examples below were used for obtaining further compounds I. The resulting compounds, together with physical data, are listed in the Tables which follow.

EXAMPLE 1

Preparation of

Stage 1:

A solution of 50 g (0.49 mol) of 2-oxobutanoic acid in 300 ml of methanol was treated with 123 g (1.47 mol) of methoxyamine hydrochloride, a little at a time. After the reaction mixture had been stirred for 16 hours at room temperature (approximately 25° C.), it was freed from solvent under reduced pressure. The resulting residue was taken up in water and tert-butyl methyl ether. The ether phase was washed with saturated NaHCO₃ solution and with water, dried over Na₂SO₄ and subsequently concentrated under reduced pressure. This gave 47 g of the title compound as a colorless liquid.

¹H NMR (CDCl₃; δ in ppm): 1.06 (t, 3H); 2.57 (q, 2H); 3.85 (s, 3H); 4.04 (s, 3H)

Stage 2:

46 g (0.32 mol) of the compound of Example 1, Stage 1, were added dropwise at 10° C. to a solution of 33 g (0.48 mol) of hydroxylamine hydrochloride and 400 ml of methanol. 171 g of sodium methoxide solution (30% strength in methanol, 0.96 mol) were subsequently added to the resulting mixture in the course of 15 minutes with ice-cooling. The reaction mixture was then stirred for 60 hours at room temperature (approximately 25° C.), during which process a suspension formed. The suspension was poured into water; the resulting mixture was acidified with concentrated hydrochloric acid, with ice-cooling, until it had reached a pH of 6.5 and subsequently extracted repeatedly with methylene chloride. The organic phases were combined, washed with water, dried over Na₂SO₄ and freed from solvent under reduced pressure at 30° C. This gave 34.1 g of the title compound as a white powder; m.p.: 56-59° C.

ATTENTION: Hydroxamic acids of the type of the compound as given in Example 1., Stage 2, may be thermolabile and decompose explosively at higher temperatures!

¹H NMR (CDCl₃; δ in ppm): 1.03 (t, 3H); 2.53 (q, 2H); 3.93 (s, 3H); 8.95 (s, br, 2H)

Stage 3:

38.6 g of sodium methoxide solution (30% strength in methanol; 0.215 mol) were added dropwise with ice-cooling to a solution of 28.5 g (0.195 mol) of the compound of Example 1, Stage 2, 55.8 g (0.195 mol) of methyl E-2-methoxyimino-2-[2′-bromomethylphenyl]acetate (in accordance with EP-A 400 417) and 600 ml of N,N-dimethylformamide. After the reaction mixture had been stirred for 16 hours at room temperature (approximately 25° C.), it was stirred into cooled dilute hydrochloric acid, and the resulting mixture was extracted with tert-butyl methyl ether. The organic phase was washed with water, dried over Na₂SO₄ and freed from solvent under reduced pressure at approximately 35° C. The residue obtained was purified by chromatography (silica gel; eluent: tert-butyl methyl ether/cyclohexane). After the solid isolated had been washed with pentane, 50 g of the title compound were obtained as a pale yellow powder; m.p.: 63-65° C.

¹H NMR (CDCl₃; δ in ppm): 1.03 (t, 3H); 2.51 (q, 2H); 3.87 (s, 6H); 4.03 (s, 3H); 4.86 (s, 2H); 7.14-7.45 (m, 4H); 8.92 (s, 1H)

Stage 4:

A mixture of 6.0 g (17.1 mmol) of the compound of Example 1, Stage 3, 22.4 g (85.5 mmol) of triphenylphosphine and 250 ml of acetonitrile was treated with 13.2 g (85.5 mmol) of tetrachloromethane, a little at a time. The resulting reaction mixture was refluxed for 60 hours and subsequently cooled to room temperature (approximately 25° C.). The solvent was distilled off under reduced pressure, and the residue which remained was purified by chromatography (silica gel, tert-butyl methyl ether/cyclohexane). This gave 2.3 g of the title compound as a beige powder; m.p.: 56-59° C.

¹H NMR (CDCl₃; δ in ppm): 0.97 (t, 3H); 2.55 (q, 2H); 3.85 (s, 3H); 3.99 (s, 3H); 4.04 (s, 3H); 5.13 (s, 2H); 7.15-7.50 (m, 4H)

EXAMPLE 2

Preparation of

A solution of 15.5 g (42 mmol) of the compound of Example 1, Stage 4, and 100 ml of tetrahydrofuran was treated with 33 g of methylamine solution (40% strength in water). After 2 hours at room temperature (approximately 25° C.), the reaction mixture was poured into cooled dilute hydrochloric acid. The acidic solution was extracted with tert-butyl methyl ether. The organic phase was subsequently washed with water, dried over Na₂SO₄ and freed from solvent under reduced pressure. After the residue had been triturated with hexane/tert-butyl methyl ether, 11.5 g of the title compound were obtained as a beige powder; m.p.: 66-69° C.

¹H NMR (CDCl₃; δ in ppm): 0.97 (t, 3H); 2.54 (q, 2H); 2.85 (d, 3H); 3.91 (s, 3H); 3.97 (s, 3H); 5.15 (s, 2H); 6.80 (s, br, 1H); 7.18-7.43 (m, 4H)

EXAMPLE 3

Preparation of

Stage 1:

A solution of 388 g (4.65 mol) of methoxyamine hydrochloride and 1.5 l of methanol was first treated with 60 g of molecular sieve (3 Å) and subsequently, at 60° C., with 254 g (1.55 mol) of methyl phenylglyoxylate. After 6 hours at 60° C. and a further 60 hours at room temperature (approximately 25° C.), the reaction mixture was treated with water. The aqueous solution was extracted with tert-butyl methyl ether. The ether phase was washed with water, dried over Na₂SO₄ and freed from solvent under reduced pressure. The residue was purified by chromatography (silica gel; tert-butyl methyl ether/cyclohexane). This gave 66 g of the title compound as a pale yellow powder.

¹H NMR (CDCl₃; δ in ppm): 3.88 (s, 3H); 4.07 (s, 3H); 7.40 (s, 5H)

Stage 2:

A solution of 36.1 g (0.52 mol) of hydroxylamine hydrochloride in 250 ml of methanol was added dropwise to a solution of 58.2 g (1.04 mol) of potassium hydroxide in 750 ml of methanol. After approximately 10 minutes, the precipitate formed was filtered off, and the resulting solution was treated with a solution of 100 g of the compound of Example 3, Stage 1, in 500 ml of methanol. After 24 hours at room temperature (approximately 25° C.), the reaction mixture was poured into water and extracted with tert-butyl methyl ether. The aqueous phase was acidified with dilute hydrochloric acid, with ice-cooling, to a pH of 6.5, during which process a precipitate formed. The precipitate was isolated and dried under reduced pressure. This gave 57 g of the title compound as a beige powder; m.p.: 142-144° C.

¹H NMR (d₆-DMSO; δ in ppm): 3.89 (s, 3H); 7.33-7.55 (m, 5H);

9.20 (s, br, 1H); 11.14 (s, br, 1H)

Stage 3:

18 g of sodium methoxide solution (30% in methanol; 0.1 mol) was added dropwise with ice-cooling to a solution of 20 g (0.1 mol) of the compound of Example 3, Stage 2, 27 g (0.1 mol) of methyl E-3-methyl-2-[2′-bromomethylphenyl]acrylate (as described in EP-A 513 580) and 300 ml of N,N-dimethylformamide. After the reaction mixture had been stirred for 12 hours at room temperature (approximately 25° C.), it was stirred into ice-water and the resulting mixture was extracted with methylene chloride. The organic phase was washed with water, dried over Na₂SO₄ and freed from solvent under reduced pressure at approximately 35° C.

The residue obtained was crystallized from tert-butyl methyl ether/hexane/isopropanol. This gave 23.8 g of the title compound as colorless crystals; m.p.: 81-84° C.

¹H NMR (CDCl₃; δ in ppm): 1.63 (d, 3H); 3.70 (s, 3H); 3.92 (s, 3H); 4.83-4.92 (m, 2H); 7.08-7.53 (m, 10H); 9.07 (s, br, 1H)

Stage 4:

A mixture of 4.8 g (12.6 mmol) of the compound of Example 3, Stage 3, 10 g (38 mmol) of triphenylphosphine and 100 ml of acetonitrile was treated with 12.6 g (38 mmol) of tetrabromomethane, a little at a time. The resulting reaction mixture was refluxed for 100 hours and subsequently cooled to room temperature (approximately 25° C.). The solvent was distilled off under reduced pressure, and the residue which remained was purified by chromatography (silica gel, tert-butyl methyl ether/cyclohexane). This gave 2.4 g of the title compound as a colorless powder; m.p.: 60-61° C.

¹H NMR (CDCl₃; δ in ppm): 1.54 (d, 3H); 3.66 (s, 3H); 3.99 (s, 3H); 5.02 (s, 2H), 7.01-7.38 (m, 10H)

TABLE I (I)

No. X Y R¹ R² R³ Physical data I.1 NOCH₃ (E) NH Cl C₆H₅ CH₃ IR (KBr): 3450, 2950, 1668, 1519, 1445, 1041, 1001, 980, 950, 930, 813, 699 cm⁻¹ I.2 CHCH₃ (E) O Br C₆H₅ CH₃ m.p.: 60-61° C. I.3 NOCH₃ (E) NH Cl CH₂CH₃ CH₃ m.p.: 66-69° C. I.4 NOCH₃ (E) O Cl CH₂CH₃ CH₃ m.p.: 56-59° C. I.5 NOCH₃ (E) O Cl CH₂CH₃ CH₂CH₃ m.p.: 81-84° C. I.6 NOCH₃ (E) NH Br CH₂CH₃ CH₂CH₃ m.p.: 68-70° C. I.7 NOCH₃ (E) NH Cl CH₂CH₃ CH₂CH₃ m.p.: 48-50° C. I.8 NOCH₃ (E) O Br CH₂CH₃ CH₂CH₃ m.p.: 42-45° C. I.9 NOCH₃ (E) O Cl 4-Cl—C₆H₄ CH₃ m.p.: 110-114° C. I.10 NOCH₃ (E) NH Cl 4-Cl—C₆H₄ CH₃ m.p.: 114-117° C. I.11 CHCH₃ (E) O Cl 4-Cl—C₆H₄ CH₃ IR(film): 1716, 1490, 1254, 1047, 1019, 1009, 956, 943, 808, 765 cm⁻¹ I.12 NOCH₃ (E) O Cl 4-F—C₆H₄ CH₃ m.p.: 111-113° C. I.13 NOCH₃ (E) NH Cl 4-F—C₆H₄ CH₃ m.p.: 121-124° C.

No. X Y R¹ R² R³ Physical data I.14 CHCH₃ (E) O Cl 4-F—C₆H₄ CH₃ m.p.: 52-55° C. I.15 CH(OCH₃) (E) O Cl CH₂CH₃ CH₃ m.p.: 75-80° C. I.16 CHCH₃ (E) O Cl CH₂CH₃ CH₃ IR(film): 1718, 1435, 1254, 1208, 1048, 1037, 1001, 946, 849, 762 cm⁻¹ I.17 NOCH₃ (E) O Cl CH₂CH₂CH₃ CH₃ IR(film): 2940, 1728, 1438, 1320, 1306, 1221, 1070, 1048, 1020, 967 cm⁻¹ I.18 NOCH₃ (E) O Cl CH₃CHCH₃ CH₃ m.p.: 98-101° C. I.19 CH(OCH₃) (E) O Cl 4-Cl—C₆H₄ propargyl IR(film): 3280, 2940, 1708, 1634, 1491, 1286, 1257, 1131, 1112, 1092, 1004, 939 cm⁻¹ I.20 NOCH₃ (E) O Cl CH₃CHCH₂CH₃ CH₃ IR(film): 2925, 2853, 1729, 1461, 1220, 1069, 1047, 1018, 969, 952 cm⁻¹ I.21 NOCH₃ (E) NH Cl CH₃CHCH₂CH₃ CH₃ IR(film): 2959, 2925, 2872, 2854, 1672 1526, 1462, 1042, 1008, 979 cm⁻¹ I.22 NOCH₃ (E) NH Cl CH₂CH₂CH₃ CH₃ m.p.: 78-81° C.

Examples for the Action Against Harmful Fungi

The improved fungicidal action of the compounds of the general formula I was demonstrated by the following experiments. The known active ingredients A.1 and A.2 were used as comparison compounds of the prior art in accordance with WO-A 95/21,153 and WO-A 95/21,154.

The active ingredients were formulated separately as a 10% emulsion in a mixture of 63% by weight of cyclohexanone and 27% by weight of emulsifier and diluted with water to give the desired concentration.

Activity Against Puccinia recondita on Wheat (Leaf Rust of Wheat)

Leaves of wheat seedlings “Fruhgold” in pots were dusted with leaf rust spores (Puccinia recondita). The pots were then placed for 24 hours into a chamber with high atmospheric humidity (90 to 95%) at 20 to 22° C. During this time, the spores germinated, and the germinal tubes penetrated the leaf tissue. The next day, the infected plants were sprayed to run-off with an aqueous preparation of the active ingredient. After the spray coating had dried on, the test plants were grown for 7 days in a greenhouse at from 20 to 22° C. and a relative atmospheric humidity of 65 to 70%. The extent of rust development on the leaves was then determined.

In this test, the plants which had been treated with 16 ppm of the compounds I.3, I.6, I.7, I.10 to I.17, I.21 and I.22 according to the invention showed no disease or a disease level of not more than 5%, while the disease level of the plants which had been treated with the same amount of the comparison compounds A.1 and A.2 was 15 and 80%, respectively. The disease level of the untreated (control) plants was 80%.

In a similar test, the plants which had been treated with 4 ppm of the compounds I.3, I.6, I.7, I.10 to I.17, I.21 and I.22 according to the invention showed a disease level of 5 to 40%, while the disease level of the comparison compounds A.1 and A.2 was 60 and 80%, respectively. The disease level of the untreated (control) plants was 80%.

Activity Against Pyricularia oryzae (Protective)

Leaves of rice seedlings cv. “Tai-Nong 67” in pots were sprayed to run-off with an aqueous preparation of the active ingredient. The next day, the plants were infected with an aqueous spore suspension of Pyricularia oryzae. The test plants were subsequently placed for 6 days into controlled-environment cabinets at 22-24° C. and a relative atmospheric humidity of 95-99%. The extent of the disease development on the leaves was then determined visually.

In this test, the plants which had been treated with 250 ppm of the compounds I.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.10, I.11, I.14 to I.17 and I.20 to I.22 according to the invention showed a disease level of not more than 15%, while the disease level of the plants which had been treated with the same amount of the comparison compounds A.1 and A.2 was 80 and 25%, respectively. The disease level of the untreated (control) plants was 80%.

Examples of the Action Against Animal Pests

The improved action of the compounds of the formula I against animal pests was demonstrated by the following experiments.

The active ingredients were formulated

a. as a 0.1% strength solution in acetone or

b. as a 10% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetter with emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Wettol® EM (non-ionic emulsifier based on ethoxylated castor oil)

and the formulations were diluted to give the desired concentration, using acetone in the case of a. or water in the case of b.

After the experiments had been concluded, in each case the lowest concentration was determined at which the compounds still caused an 80 to 100% inhibition or mortality in comparison with untreated controls (limit or minimal concentration). 

We claim:
 1. A hydroximic acid halide compound I

wherein the substituents have the following meanings: X is NOCH₃, CHOCH₃ or CHCH₃; Y is O or NH; R¹ is halogen; R² is C₂-C₆-alkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl, it being possible for these groups to be partially or fully halogenated and/or to have attached to them one or two of the following radicals: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and phenyl, it being possible for the phenyl, in turn, to be partially or fully halogenated and/or to have attached to it one to three of the following groups: cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; methyl which is partially or fully halogenated and/or has attached to it one of the following radicals: cyano, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; C₅-C₆-cycloalkyl which can be partially or fully halogenated and/or can have attached to it one to three C₁-C₄-alkyl groups; aryl or arylmethylene which can be partially or fully halogenated in the aryl moiety and/or can have attached to it one to three of the following radicals: cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R³ is C₁-C₆-alkyl, C₁-C₃-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₃-C₆-alkenyl and C₃-C₆-alkynyl, it being possible for these groups to be partially or fully halogenated and it being possible for the cycloalkyl groups additionally to have attached to them one to three C₁-C₄-alkyl radicals, or a salt thereof.
 2. A process for the preparation of the compound I defined in claim 1, which comprises first converting a carboxylic ester IIa

wherein R^(x) is C₁-C₆-alkyl or phenyl, with hydroxylamine to give the corresponding hydroxamic acid IIc

subsequently reacting IIc with a benzyl compound IIIa

wherein L is a nucleofugic leaving group, to give a hydroxamic ester compound IV

and converting IV with a halogenating agent to give the compound I.
 3. A process for the preparation of the compound IV set forth in claim 2, which comprises reacting a carboxylic acid IIb

with a benzylhydroxylamine IIIb


4. A process for the preparation of the compound I defined in claim 1, which comprises converting an amidoxime IId

with a benzyl compound IIIa

to give a compound V

and exchanging the amino group of V for halogen via a diazotization reaction.
 5. A composition which is suitable for controlling animal pests or harmful fungi, comprising a solid or liquid carrier and the compound I defined in claim
 1. 6. A method of controlling harmful fungi, which comprises treating the fungi, or the materials, plants, soil or seeds to be protected against fungal infection with an effective amount of the compound I defined in claim
 1. 7. A method of controlling animal pests, which comprises treating the pests or the materials, plants, soil or seeds to be protected against the animal pests with an effective amount of the compound I defined in claim
 1. 8. The compound I defined in claim 1, wherein X is NOCH₃, Y is NH, R¹ is chlorine and R³ is C₁-C₃-alkyl.
 9. The compound I defined in claim 1, wherein R² is C₂-C₆-alkyl.
 10. The compound I defined in claim 1, wherein R² is phenyl which is unsubstituted, or is partially halogenated and/or carries one to three radicals selected from the group consisting of cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, or which phenyl is fully halogenated.
 11. The compound I defined in claim 8, wherein R² is C₂-C₆-alkyl.
 12. The compound I defined in claim 8, wherein R² is phenyl which is unsubstituted, or is partially halogenated and/or carries one to three radicals selected from the group consisting of cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, or which phenyl is fully halogenated. 